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$68 Find cheap flights from San Diego to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Diego to Chicago departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/22
Sat 6/29

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Chicago.
In the last 7 days travelers have searched 43,800,826 times on KAYAK, and here is why:

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Cheap flight deals from San Diego to Chicago (SAN-CHI)

 
These are the cheapest deals for flights from San Diego to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from San Diego to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from San Diego to Chicago.

Recent one-way flight deals from San Diego to Chicago

Only flying one-way? Below are some of the best one-way flight deals from San Diego to Chicago found on KAYAK recently.

Recent last minute flight deals from San Diego to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from San Diego to Chicago.

Recent direct flight deals from San Diego to Chicago

The latest deals for direct flights from San Diego to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from San Diego to Chicago

Find recent round-trip train or bus tickets from San Diego to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:21 pm - 5:00 amSAN-ORD
6h 39m1 stop
9:53 pm - 7:01 amORD-SAN
11h 08m1 stop
$140Frontier
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Tue, Jun 4 - Wed, Jun 5
8:21 pm - 5:29 amSAN-MDW
7h 08m1 stop
10:26 pm - 7:01 amMDW-SAN
10h 35m1 stop
$140Frontier
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Wed, Jun 5 - Sat, Jun 8
8:14 am - 11:50 pmSAN-ORD
13h 36m1 stop
2:57 pm - 10:02 amORD-SAN
21h 05m2 stops
$144Spirit Airlines
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Wed, Jun 5 - Tue, Jun 11
8:21 pm - 5:23 amSAN-ORD
7h 02m1 stop
8:23 pm - 5:08 pmORD-SAN
22h 45m1 stop
$146Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
8:21 pm - 5:29 amSAN-MDW
7h 08m1 stop
8:02 pm - 5:08 pmMDW-SAN
23h 06m1 stop
$146Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
8:45 am - 8:00 pmSAN-ORD
9h 15m1 stop
2:57 pm - 7:24 amORD-SAN
18h 27m1 stop
$158Spirit Airlines
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Fri, Jun 7 - Mon, Jun 10
8:24 pm - 5:25 amSAN-ORD
7h 01m1 stop
10:01 pm - 8:34 amORD-SAN
12h 33m1 stop
Tue, Jun 11 - Tue, Jun 18
8:24 pm - 5:34 amSAN-ORD
7h 10m1 stop
2:57 pm - 7:24 amORD-SAN
18h 27m1 stop
Sat, Jun 15 - Tue, Jun 25
10:15 pm - 8:45 amSAN-MDW
8h 30m1 stop
6:45 pm - 11:39 pmMDW-SAN
6h 54m1 stop
$308Delta
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Tue, Oct 8 - Tue, Oct 15
10:15 pm - 8:45 amSAN-MDW
8h 30m1 stop
6:45 pm - 11:39 pmMDW-SAN
6h 54m1 stop
$318Delta
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Fri, Oct 11 - Tue, Oct 15
9:00 am - 11:58 pmSAN-ORD
12h 58m1 stop
$68Spirit Airlines
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Tue, Aug 20
8:21 pm - 5:00 amSAN-ORD
6h 39m1 stop
$70Frontier
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Tue, Jun 4
10:52 pm - 5:00 amSAN-ORD
4h 08mnonstop
$151American Airlines
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Fri, Jun 14
10:52 pm - 5:00 amSAN-ORD
4h 08mnonstop
$171American Airlines
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Mon, Jun 10
4:40 pm - 10:44 pmSAN-ORD
4h 04mnonstop
$184United Airlines
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Tue, Aug 20
10:05 pm - 8:38 amSAN-MDW
8h 33m1 stop
$193Delta
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Tue, Jul 23
10:29 pm - 4:40 amSAN-ORD
4h 11mnonstop
$229United Airlines
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Tue, Jul 9
10:05 pm - 8:38 amSAN-MDW
8h 33m1 stop
$235Delta
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Fri, Jul 26
8:24 am - 11:37 pmSAN-ORD
13h 13m2 stops
$361Alaska Airlines
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Sun, Sep 8
10:45 pm - 5:00 amSAN-ORD
4h 15mnonstop
$399Alaska Airlines
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Sun, Sep 8
2:39 pm - 11:09 amSAN-MDW
18h 30m1 stop
2:45 pm - 9:25 pmMDW-SAN
8h 40m1 stop
$162Frontier
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Tue, May 28 - Tue, Jun 4
8:21 pm - 5:00 amSAN-ORD
6h 39m1 stop
7:59 pm - 2:40 pmORD-SAN
20h 41m1 stop
$180Frontier
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Sat, May 25 - Wed, May 29
9:12 pm - 9:55 pmSAN-ORD
22h 43m1 stop
7:52 pm - 1:48 pmORD-SAN
19h 56m2 stops
$263Spirit Airlines
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Tue, May 28 - Mon, Jun 3
8:07 pm - 6:40 amSAN-ORD
8h 33m1 stop
10:57 pm - 1:15 pmORD-SAN
16h 18m2 stops
$312Spirit Airlines
Find Deal
Sat, May 25 - Wed, May 29
8:00 am - 2:10 pmSAN-ORD
4h 10mnonstop
1:40 pm - 9:41 pmORD-SAN
10h 01m1 stop
$467American Airlines
Find Deal
Tue, May 28 - Wed, May 29
10:57 pm - 5:00 amSAN-ORD
4h 03mnonstop
6:39 pm - 9:06 pmORD-SAN
4h 27mnonstop
$479American Airlines
Find Deal
Fri, May 24 - Tue, Jun 25
5:30 pm - 4:40 amSAN-ORD
9h 10m1 stop
3:50 pm - 10:45 pmORD-SAN
8h 55m1 stop
$693Alaska Airlines
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Fri, May 24 - Fri, May 31
10:40 am - 4:56 pmSAN-ORD
4h 16mnonstop
7:18 am - 9:36 amORD-SAN
4h 18mnonstop
$744United Airlines
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Sun, May 26 - Sun, Jun 2
10:29 pm - 4:40 amSAN-ORD
4h 11mnonstop
5:04 am - 9:32 amORD-SAN
6h 28m1 stop
$754United Airlines
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Sun, May 26 - Sun, Jun 2
11:35 am - 5:45 pmSAN-ORD
4h 10mnonstop
3:50 pm - 11:59 pmORD-SAN
10h 09m1 stop
$789Alaska Airlines
Find Deal
Fri, May 24 - Fri, May 31
10:52 pm - 5:00 amSAN-ORD
4h 08mnonstop
6:39 pm - 9:06 pmORD-SAN
4h 27mnonstop
$300American Airlines
Find Deal
Sun, Jun 16 - Fri, Jun 21
10:52 pm - 5:00 amSAN-ORD
4h 08mnonstop
6:39 pm - 9:06 pmORD-SAN
4h 27mnonstop
$301American Airlines
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Thu, Jun 13 - Mon, Jun 17
6:21 am - 12:37 pmSAN-ORD
4h 16mnonstop
6:39 pm - 9:06 pmORD-SAN
4h 27mnonstop
$302American Airlines
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Sun, Jun 16 - Fri, Jun 21
10:29 pm - 4:40 amSAN-ORD
4h 11mnonstop
7:18 am - 9:36 amORD-SAN
4h 18mnonstop
$321United Airlines
Find Deal
Mon, Jun 10 - Wed, Jun 12
10:52 pm - 5:00 amSAN-ORD
4h 08mnonstop
6:39 pm - 9:06 pmORD-SAN
4h 27mnonstop
$334American Airlines
Find Deal
Tue, Jun 18 - Sat, Jun 22
10:52 pm - 5:00 amSAN-ORD
4h 08mnonstop
6:39 pm - 9:06 pmORD-SAN
4h 27mnonstop
$346American Airlines
Find Deal
Fri, Jun 21 - Fri, Jun 28
4:45 pm - 10:56 pmSAN-ORD
4h 11mnonstop
8:50 am - 11:08 amORD-SAN
4h 18mnonstop
$366United Airlines
Find Deal
Thu, Jun 6 - Tue, Jun 11
6:20 am - 12:36 pmSAN-ORD
4h 16mnonstop
8:05 pm - 10:24 pmORD-SAN
4h 19mnonstop
$382United Airlines
Find Deal
Sat, Jun 22 - Sat, Jun 22
10:29 pm - 4:40 amSAN-ORD
4h 11mnonstop
7:18 am - 9:36 amORD-SAN
4h 18mnonstop
$391United Airlines
Find Deal
Thu, Jun 20 - Sun, Jun 23
10:52 pm - 5:00 amSAN-ORD
4h 08mnonstop
4:51 pm - 7:01 pmORD-SAN
4h 10mnonstop
$1,188Alaska Airlines
Find Deal
Sat, Jun 8 - Mon, Jun 17

Flights from San Diego to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from San Diego to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest San Diego to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from San Diego to Chicago.
Our data shows that the cheapest route for a one-way flight from San Diego to Chicago cost $164 and was between San Diego and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $286.

What’s the cheapest day of the week to fly from San Diego to Chicago?

The average price of all flights from San Diego to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from San Diego to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

What is the cheapest month to fly from San Diego to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San Diego to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from San Diego to Chicago is September, where tickets cost $307 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $462 and $442 respectively.

How far in advance should I book a flight from San Diego to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from San Diego to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from San Diego to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 78 days before departure.

Which airlines provide the cheapest flights from San Diego to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from San Diego to Chicago found on KAYAK was with Spirit Airlines for $68. Frontier proposed a round-trip connection from $140 and Spirit Airlines from $144.

Which airlines fly most frequently between San Diego and Chicago?

San Diego and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (6 flights per day), Southwest (5 flights per day), and American Airlines (4 flights per day).

Which airlines fly non-stop between San Diego and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from San Diego to Chicago.
There are 3 airlines that fly nonstop from San Diego to Chicago. They are: American Airlines, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $218 for a one-way flight. On average, the best prices for this route can be found at United Airlines.

How many flights are there between San Diego and Chicago per day?

Each day, there are between 14 and 19 nonstop flights that take off from San Diego and land in Chicago, with an average flight time of 4h 04m. The most common departure time is 6:00 am and most flights take off in the morning, while the most flights land at Chicago Midway Airport. Each week, there are 119 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between San Diego and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from San Diego to Chicago take?

Direct flights cover the 1,732 miles separating San Diego to Chicago in about 4h 03m.

What’s the earliest departure time from San Diego to Chicago?

Early birds can take the earliest flight from San Diego at 6:20 am and will be landing in Chicago at 12:36 pm.

What’s the latest departure time from San Diego to Chicago?

If you prefer to fly at night, the latest flight from San Diego to Chicago jets off at 10:57 pm and lands at 5:00 am.

Good to know

Low season

January

High season

June

Cheapest flight

$68
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from San Diego to Chicago O'Hare Airport

When to book flights from San Diego to Chicago

Are your dates flexible? Find out the best times to travel from San Diego to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from San Diego to Chicago

  • How can I rent a car when I arrive at Chicago O'Hare International Airport (ORD)?

    All of the major rental car companies have locations at the Multi-Modal Facility located offsite from the airport. Dedicated shuttle buses run 24/7 from the airport terminals to the facility. Pickup locations for the shuttle buses are clearly marked with locations just outside of the terminal baggage claim areas.

  • Are there nonstop flights from San Diego International Airport (SAN) to Chicago?

    There are several nonstop flight choices from Chicago to San Diego. Southwest Airlines offers nonstop service to Chicago Midway Airport (MDW), while both United Airlines and American Airlines offer nonstop service to Chicago O'Hare International Airport (ORD).

  • What is a good way to get from Chicago O'Hare International Airport (ORD) to the city center by public transportation?

    The Chicago Transit Authority offers a train service from the airport. The Blue Line train operates on a 24h basis, making several stops on the way, with both the Clinton and Grand stops being great places to hop off the train in Downtown Chicago.

  • Is there a public transportation option to get from Chicago Midway Airport (MDW) to the city center?

    The Chicago Transit Authority's Orange Line offers service to Chicago Midway Airport. The trains run from early morning until after midnight every day. The trip to Downtown Chicago from the airport takes roughly 25min. The Roosevelt Station is a great place to hop off the train to explore Downtown Chicago.

  • What is the cheapest flight from San Diego to Chicago?

    In the last 3 days, the lowest price for a flight from San Diego to Chicago was $68 for a one-way ticket and $140 for a round-trip.

  • Do I need a passport to fly between San Diego and Chicago?

    No

  • Which airports will I be using when flying from San Diego to Chicago?

    On your way to Chicago, you’ll fly out from San Diego. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from San Diego to Chicago?

    All the following airlines offer inflight Wi-Fi service on the San Diego to Chicago flight route: American Airlines, Alaska Airlines, JetBlue, Delta, Air Canada, Lufthansa, and United Airlines.

  • Which aircraft models fly most regularly from San Diego to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the San Diego to Chicago flight route.

  • Which airline alliances offer flights from San Diego to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between San Diego and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from San Diego to Chicago?

    There are nonstop flights from San Diego to Chicago on a daily basis.

  • Which is the best airline for flights from San Diego to Chicago, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from San Diego to Chicago are Alaska Airlines and Delta. With an average price for the route of $517 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $386 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from San Diego to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Diego to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Diego to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Diego is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Diego to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to San Diego with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Diego to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from San Diego up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from San Diego to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $225 or less one-way and $410 or less round-trip.
  • If you’re looking for something to eat after your flight from San Diego, Chicago Midway Airport (MDW) offers a wide variety of choices. This includes everything from quick and simple options like Einstein Brothers Bagels and Dunkin Express to the artisan pizza found at Woodgrain Neapolitan Pizza.
  • The city bus 992 offers service between Downtown San Diego and San Diego International Airport (SAN). The bus operates from early in the morning until almost midnight and offers buses every 15min during the week and every 30min on weekends and holidays.
  • If you are looking for a place to wait before your flight to Chicago, stop in at the Airspace Lounge located in Terminal 2 of San Diego International Airport. For a fee between $20 and $30 per hour, you can enjoy a host of amenities, including a wide array of food and beverage choices, plus restrooms, showers, and an abundant seating area.
  • Are you planning on driving yourself to San Diego International Airport before your flight to Chicago? There are parking lots located at both terminal buildings. Both of the lots offer an hourly rate for the first 24h and then offer daily rates after that. The lots are adjacent to each terminal building and the terminals are easily accessed by a covered walkway.
  • If you’ve forgotten your favorite entertainment or technology device for the flight from San Diego to Chicago, there are two Best Buy Express vending machines located at San Diego International Airport. These machines carry things like chargers for mobile phones, noise-canceling headphones, and digital cameras.
See more tips

Prefer to fly non-stop from San Diego to Chicago?

Find which airlines fly direct from San Diego to Chicago, which days they fly and book direct flights.

Nonstop departures

San Diego to Chicago

Monday

Aer Lingus, Air Canada, Alaska Airlines, +14 more

Aer Lingus, Air Canada, +15 more

Tuesday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Wednesday

Aer Lingus, Air Canada, Alaska Airlines, +15 more

Aer Lingus, Air Canada, +16 more

Thursday

Aer Lingus, Air Canada, Alaska Airlines, +15 more

Aer Lingus, Air Canada, +16 more

Friday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Saturday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Sunday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

See more direct flights

Nonstop returns

Chicago to San Diego

Monday

Aer Lingus, Air Canada, Alaska Airlines, +15 more

Aer Lingus, Air Canada, +16 more

Tuesday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Wednesday

Aer Lingus, Air Canada, Alaska Airlines, +15 more

Aer Lingus, Air Canada, +16 more

Thursday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Friday

Aer Lingus, Air Canada, Alaska Airlines, +15 more

Aer Lingus, Air Canada, +16 more

Saturday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Sunday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

See more direct flights
See more direct flights

Top 5 airlines serving from San Diego to Chicago

 
See real verified KAYAK customer reviews for airlines flying from San Diego to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Diego to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9175 reviews
7.3Food
7.9Comfort
7.3Entertainment
8.6Crew
8.2Boarding
Airline reviews

It was ok. Alaska was adequate. Efficient and what I paid for it was fair. The boarding area at the gate was a joke. By the time they get past the C boarding group people all line up impatiently and then it’s chaos. We were boarding early then we sat on the tarmac for 30 minutes. I would of rather sat in the airport.

6.0 GoodAnonymous, May 2024SAN - PDX
Read more about Alaska Airlines reviews

It was ok. Alaska was adequate. Efficient and what I paid for it was fair. The boarding area at the gate was a joke. By the time they get past the C boarding group people all line up impatiently and then it’s chaos. We were boarding early then we sat on the tarmac for 30 minutes. I would of rather sat in the airport.

Pilot warned us it was going to be bumpy, which I usually like when it is, but it wasn't, so I spent most of the flight unnecessarily wondering when it was going to get rough. Just can't win sometimes. Ha!

Flight itself was great! Snacks are never really good; in this case, the "butter braids" and Biscotti cookie were both hard. The attendants' were good. We felt we found a good deal on the cost. The check-in process was very smooth: Alaskan Airlines always does a good job. Boarding was pretty timely, too. We fly Alaskan whenever possible and will continue to do so.

The space for legs in coach is better than other Airlines you can even cross your legs!!

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

I really like Alaska airline, it's my favorite airline❤️

Alaska Airlines was fantastic. Kayak on the other hand was extremely poor. I got tickets through Kayak for a flight to a funeral. The date got changed less than 12 hours after I made my reservations. When I attempted to change my flights through Kayak, I was unable to use either the website or the phone system. The phone matrix did not give an option to cancel or change. The website said Kayak could not find any record of me making airline reservations through Kayak and even through I never left the Kayak website when making the reservations to my knowledge. After more than a half hour of frustration on the phone and computer ( on top of dealing with the death of a member of my family) I finally contacted Alaska Airline directly and they cancelled my flight and refunded the cost very quickly and efficiently. Alaska Airlines gets 10 stars. Kayak gets zero stars and has permanently lost a customer. I will never use Kayak again.

My plane ride down landed 20 min late. Boarding at SFO was strange too. The people at the terminal were nice—but, boarding lacked direction, and was confusing . Coming back was worse—the plane was hours behind—and I barely caught the last Bart train back to San Francisco (3 min more and I would have been in trouble). It was a very stressful trip, and it didn’t need to be.

This flight was significantly affected by poor wifi connections. I couldn’t get my work done because the wifi kept dropping. Even texts were not going through. There is no seat power in premium class either. I fly a lot. Today was my 10th flight in 4 weeks. This was by far the only flight that was sub par.

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Horrible - they lied to me about baggage & boarding, even though I specifically spoke to their agents the day before my flight about my issue. When I showed up they did not let me board and stranded me at my airport until I bought a new flight with money I did not have to spend.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

I felt scam to have to pay $50 additional for my carry on luggage which was free for my other airline.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

Book cheap flights from San Diego to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Diego to Chicago found on KAYAK in the last 72 hours.
8/20Tue
1 stopSpirit Airlines
12h 58mSAN-ORD
$68
6/4Tue
1 stopFrontier
6h 39mSAN-ORD
$70
6/14Fri
nonstopAmerican Airlines
4h 08mSAN-ORD
$151
6/10Mon
nonstopAmerican Airlines
4h 08mSAN-ORD
$171
8/20Tue
nonstopUnited Airlines
4h 04mSAN-ORD
$184
7/23Tue
1 stopDelta
8h 33mSAN-MDW
$193
7/9Tue
nonstopUnited Airlines
4h 11mSAN-ORD
$229
7/26Fri
1 stopDelta
8h 33mSAN-MDW
$235
9/8Sun
2 stopsAlaska Airlines
13h 13mSAN-ORD
$361
9/8Sun
nonstopAlaska Airlines
4h 15mSAN-ORD
$399

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Last minute flights from San Diego to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from San Diego to Chicago that are departing in the next 10 days.
5/28Tue
multi-stopFrontier
18h 30mSAN-MDW
6/4Tue
multi-stopFrontier
8h 40mMDW-SAN
$162
5/25Sat
multi-stopFrontier
6h 39mSAN-ORD
5/29Wed
multi-stopFrontier
20h 41mORD-SAN
$180
5/28Tue
multi-stopSpirit Airlines
22h 43mSAN-ORD
6/3Mon
multi-stopSpirit Airlines
19h 56mORD-SAN
$263
5/25Sat
multi-stopSpirit Airlines
8h 33mSAN-ORD
5/29Wed
multi-stopSpirit Airlines
16h 18mORD-SAN
$312
5/28Tue
nonstopAmerican Airlines
4h 10mSAN-ORD
5/29Wed
multi-stopAmerican Airlines
10h 01mORD-SAN
$467
5/24Fri
nonstopAmerican Airlines
4h 03mSAN-ORD
6/25Tue
nonstopAmerican Airlines
4h 27mORD-SAN
$479
5/24Fri
multi-stopAlaska Airlines
9h 10mSAN-ORD
5/31Fri
multi-stopAlaska Airlines
8h 55mORD-SAN
$693
5/26Sun
nonstopUnited Airlines
4h 16mSAN-ORD
6/2Sun
nonstopUnited Airlines
4h 18mORD-SAN
$744
5/26Sun
nonstopUnited Airlines
4h 11mSAN-ORD
6/2Sun
multi-stopUnited Airlines
6h 28mORD-SAN
$754
5/24Fri
nonstopAlaska Airlines
4h 10mSAN-ORD
5/31Fri
multi-stopAlaska Airlines
10h 09mORD-SAN
$789

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San Diego - Chicago Flights

Departure:

San Diego (SAN)United States

Return flight deals:

Chicago - San Diego

Cabin classes:

$942
$951
$1,559
$286