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Find First Class Flights to Chicago

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Fri 6/7
Fri 6/14

Good to Know - First Class Flights to Chicago

Low season

January

High season

May

Average price round-trip

$3,054

Good deal round-trip

$568

Good deal one-way

$311
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 5% lower on average.
(avg. price over the last 2 weeks)
or less
or less

When to book first class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago, so you can find the best time to fly.
Average price per month
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all the values for each month.
Flight prices as travel date approaches
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.

FAQs for Chicago first class flights

  • Which airline has the best first class amenities for flights to Chicago?

    If you reserve a first class flight to Chicago using American Airlines, you will have access to some of the world's best amenities. These range from their cozy, spacious, and luxurious seats to delicious meals and unlimited entertainment. First class passengers use seats with more legroom, ensuring their comfort the entire journey. Passengers are also served a variety of freshly prepared meals accompanied by drinks.

  • Which airline has the best flatbeds for first class flights to Chicago?

    American Airlines has the best flatbeds for first class flights to Chicago. The passengers are able to conveniently adjust their seats to a fully horizontal position. Their property of being spacious makes it possible for them to take any shape. Additionally, the process of adjusting the position of the seat is quite easy; the passenger is only required to press the adjust button, and everything is done.

  • Which airline has the best first class lounge amenities for flights to Chicago?

    The American Airlines' first class lounge has the best amenities. These include the spacious dining where passengers enjoy a variety of freshly prepared meals served with a rich selection of drinks. The lounge also has large flat-screen televisions that offer them unlimited entertainment as they wait for the plane.

  • What is the most popular airline offering First Class flights to Chicago?

    Among KAYAK users, American Airlines is the most popular airline offering First Class seats on flights to Chicago.

  • Which airlines offer First Class tickets on flights to Chicago?

    Traveling to Chicago and want to offer yourself a First Class experience? Depending on the origin, the following airlines offer seats in First Class: American Airlines, United Airlines, Alaska Airlines and Delta.

  • How does KAYAK find such good deals on First Class tickets to Chicago?

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

  • What is the best airline for first class flights to Chicago?

    The highest-rated airline by KAYAK users offering first class flights to Chicago is Delta, with an overall rating of 8.0.

See more FAQs

Top tips for finding first class flights to Chicago

  • Booking first class flights to Chicago through the Chicago O' Hare International Airport and Chicago Midway International Airport will give you the advantage of a shorter security line. This will ensure that you do not waste time before getting to your luxurious seat.
  • Travelers at the Chicago O' Hare International Airport will be able to access the first class lounge at Terminal 3. Those at the Chicago Midway International Airport will be able to access the first-class lounge at Terminal 1.
  • Passengers using first class flights to Chicago will be the first to alight when their plane lands at Chicago O' Hare International Airport or Chicago Midway International Airport. Their luggage will also undergo security checks before that of the other passengers. This increases their level of convenience.
  • The most expensive day to fly First Class to Chicago is Sunday, while the cheapest is Friday.
  • To get a below average price, try to book at least 1 week in advance of your departure date.
See more tips

Top 5 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the United States to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly first class 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.
8.1
SouthwestOverall score based on 6075 reviews
8.3Boarding
7.8Entertainment
8.7Crew
8.1Comfort
7.3Food
Airline reviews

Southwest is going downhill. I'm more apt to fly other airlines now. And I'd appreciate it if your gate agents didn't invent non-existent laws. If Southwest is having issues getting flight crews, you need to go out of your way to accommodate passengers instead of saying it's weather related and not in your hands. We can all see the other carriers are getting their planes off the ground and to/from the cities/regions you claim are weather-impacted.

8.0 ExcellentBrian, May 2024BNA - TPA
Read more about Southwest reviews

Southwest is going downhill. I'm more apt to fly other airlines now. And I'd appreciate it if your gate agents didn't invent non-existent laws. If Southwest is having issues getting flight crews, you need to go out of your way to accommodate passengers instead of saying it's weather related and not in your hands. We can all see the other carriers are getting their planes off the ground and to/from the cities/regions you claim are weather-impacted.

Southwest is a discount airline. I get it. You take the (usually) good pricing with the bad (cramped). But Southwest is becoming more and more like the cut-rate airlines *cough* Spirit *cough*. It used to actually be a fun experience. e.g. paying for WiFi is bad enough - having to pay for it on each leg of a flight is ridiculous. Yes, I've seen your numbers that it only "impacts a small percentage", but you and I both know that is misleading at best. While I used to try to fly SW exclusively when flying domestically, now I'll look elsewhere very frequently and price being equal (or close) I'm going to the other carriers.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

The flight itself was good. Delays were the problem. Original flight was scheduled for 8:10 pm. Got notifications all day -- actual time is 8:40; then 8:25; then 8:35; then 8:45. Then once I get through security, it's actually 9:35.

Crew was great but because of fog they diverted us to Ontario instead of our Santa Barbara destination. Instead of cancelling the flight as soon as we landed in Ontario, they instead held us in Ontario for almost 4 hours before cancelling the flight. I had to rent a car in Ontario to get back to ventura on time to get an elderly relative his medication and take over his caretaking… otherwise if I had taken the buses you offered from Ontario I wouldn’t have even arrived to Santa Barbara till at least midnight (according to southwest airlines employees at Ontario), and then would have had to drive back down to ventura. At least renting the car I could get up to ventura by 10 pm to take care of my loved one.

Boarding was quick. The flight itself was good. However, no charging ports for cell phones. Also, the food provided was just a few snacks. For a 5-hr flight, I would expect at least a sandwich.

Landing was kinda fast and my ears were plugged for days after.

Healthier snack would be much appreciated. Love traveling on Southwest!

We sat on the tarmac for 2 hours waiting in line to be de-iced. The flight is 1.5 hours, so we spent more time tied to our seats for no reason than actually flying.

Best domestic airline in the USA. Excellent fares and two bags included with every fare (only carrier to do so).

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

Everything was fine -- on time, clear, clean. I don't want to pay extra for in-flight wi-fi

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

I bought the cheapest ticket. No meal, no checked luggage so I didn't expect much and was surprised by how good the flight and service was. Alaska is now my favorite airline.

No entertainment, food was cookies & juice,water, soda or coffee.

My baggage was in another flight, anit was delayed for one hour.

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

The only issue was in the wheelchair waiting area before we got on the plane. They seemed very disorganized. Everyone we encountered after that was great! We loved Cassandra at check-in. She was awesome. The flight attendants were wonderful too! The lady helping with the waiting wheelchair when we got off the plane was awesome too!

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Everything was good except for deplaning in NY. Took way too long!!

Jet Blue keeps getting iit wrong. 4 hour mechanical delay followed by terrible boarding experience. This is my third horrific jet blue flight in 2024. I am going to try to avoid this loser in the sky

Wish we had music during take off and landing like the last flight

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Book first class plane tickets to Chicago

Recent round-trip first class deals

 
We’ve provided our cheapest round-trip first class flights to Chicago found on KAYAK in the last 72 hours.
6/11Tue
nonstopDelta
2h 51mBOS-ORD
6/12Wed
nonstopDelta
2h 28mORD-BOS
$391
6/15Sat
1 stopAmerican Airlines
26h 00mLGA-ORD
6/16Sun
nonstopAmerican Airlines
2h 12mORD-LGA
$393
10/8Tue
nonstopDelta
3h 02mJFK-ORD
10/9Wed
nonstopDelta
2h 20mORD-JFK
$399
7/4Thu
nonstopDelta
2h 58mJFK-ORD
7/10Wed
nonstopDelta
2h 14mORD-JFK
$408
10/8Tue
nonstopDelta
2h 49mBOS-ORD
10/9Wed
nonstopDelta
2h 28mORD-BOS
$409
10/8Tue
nonstopDelta
2h 49mBOS-ORD
10/12Sat
nonstopDelta
2h 24mORD-BOS
$414
10/5Sat
nonstopDelta
2h 47mJFK-ORD
10/8Tue
nonstopDelta
2h 47mORD-JFK
$422
10/9Wed
nonstopDelta
2h 50mBOS-ORD
10/12Sat
nonstopDelta
2h 24mORD-BOS
$434
6/11Tue
1 stopDelta
6h 27mBOS-ORD
6/12Wed
nonstopDelta
2h 28mORD-BOS
$435
6/19Wed
nonstopDelta
2h 45mJFK-ORD
7/20Sat
nonstopDelta
2h 38mORD-JFK
$441
10/5Sat
nonstopDelta
3h 05mJFK-ORD
10/12Sat
nonstopDelta
2h 20mORD-JFK
$445
6/3Mon
nonstopAmerican Airlines
2h 35mLGA-ORD
6/5Wed
1 stopAmerican Airlines
3h 43mORD-LGA
$449
10/5Sat
nonstopUnited Airlines
2h 43mBOS-ORD
10/9Wed
nonstopUnited Airlines
2h 29mORD-BOS
$449
7/22Mon
nonstopDelta
3h 01mJFK-ORD
8/12Mon
nonstopDelta
2h 47mORD-JFK
$453
10/5Sat
nonstopUnited Airlines
2h 43mBOS-ORD
10/12Sat
nonstopUnited Airlines
2h 29mORD-BOS
$454
10/8Tue
1 stopUnited Airlines
4h 51mBOS-ORD
10/8Tue
nonstopUnited Airlines
2h 29mORD-BOS
$458
10/5Sat
1 stopUnited Airlines
5h 57mBOS-ORD
10/12Sat
nonstopUnited Airlines
2h 29mORD-BOS
$459
10/4Fri
1 stopUnited Airlines
5h 27mBOS-ORD
10/8Tue
nonstopUnited Airlines
2h 29mORD-BOS
$463
10/4Fri
1 stopUnited Airlines
5h 27mBOS-ORD
10/6Sun
nonstopUnited Airlines
2h 26mORD-BOS
$468
6/19Wed
nonstopDelta
2h 45mJFK-ORD
7/23Tue
nonstopDelta
2h 14mORD-JFK
$470

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Recent one-way first class deals

 
Only flying one-way? Below are some of the best deals for one-way first class flights to Chicago found on KAYAK in the last 72 hours.
6/1Sat
nonstopDelta
2h 51mJFK-ORD
$190
9/5Thu
nonstopDelta
2h 50mBOS-ORD
$190
6/3Mon
nonstopDelta
2h 51mJFK-ORD
$200
6/5Wed
nonstopUnited Airlines
2h 50mBOS-ORD
$204
6/13Thu
nonstopDelta
2h 52mBOS-ORD
$210
5/15Wed
nonstopDelta
2h 42mJFK-ORD
$215
6/2Sun
nonstopDelta
2h 42mJFK-ORD
$219
6/5Wed
1 stopUnited Airlines
4h 50mBOS-ORD
$223
6/2Sun
nonstopAmerican Airlines
2h 52mBOS-ORD
$226
7/14Sun
nonstopUnited Airlines
2h 46mBOS-ORD
$230
6/11Tue
nonstopAmerican Airlines
4h 00mSEA-ORD
$240
5/27Mon
nonstopUnited Airlines
2h 35mLGA-ORD
$243
5/21Tue
nonstopDelta
2h 51mJFK-ORD
$249
6/11Tue
1 stopAmerican Airlines
7h 48mSEA-ORD
$249
6/1Sat
nonstopUnited Airlines
2h 35mLGA-ORD
$249
5/16Thu
nonstopDelta
2h 55mBOS-ORD
$249
6/2Sun
1 stopAmerican Airlines
4h 28mBOS-ORD
$250
5/27Mon
nonstopUnited Airlines
2h 35mEWR-ORD
$253
8/24Sat
nonstopUnited Airlines
2h 38mEWR-ORD
$254
6/1Sat
nonstopDelta
4h 06mSEA-ORD
$255

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$333
$301
$219
$38

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