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Find cheap flights from Chicago to Rehoboth Beach from $33

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Rehoboth Beach departing on 5/29. 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

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Good to know

Low season

January

High season

May

Cheapest flight

$33
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Chicago O'Hare Airport to Philadelphia

When to book flights from Chicago to Rehoboth Beach

Are your dates flexible? Find out the best times to travel from Chicago to Rehoboth Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Rehoboth Beach

  • Which airports will I be using when flying from Chicago to Rehoboth Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Rehoboth Beach does not have its own airport so you’ll be flying into nearby Philadelphia airport, which is 80.4 mi away.

  • How long does a flight from Chicago to Rehoboth Beach take?

    Direct flights cover the 661 miles separating Chicago and Rehoboth Beach in about 1h 59m.

  • How many flights are there between Chicago and Rehoboth Beach?

    66 direct flights run between Chicago and Rehoboth Beach on a daily basis. On average, there are about 464 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Rehoboth Beach?

    Consider leaving on a Wednesday and avoid Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Fridays.

  • How does KAYAK find such low prices on flights from Chicago to Rehoboth Beach?

    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 Chicago to Rehoboth Beach.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Rehoboth Beach from Chicago 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 Chicago to Rehoboth Beach?

    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 Rehoboth Beach with an airline and back to Chicago with another airline.

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

    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 Rehoboth Beach from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Rehoboth Beach?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Rehoboth Beach found on KAYAK was with Frontier for $33. Frontier offered a round-trip connection from $57 and Spirit Airlines from $123.

See more FAQs

Top tips for finding cheap flights from Chicago to Rehoboth Beach

  • There is no airport in Rehoboth Beach. Instead, you’ll be flying into Philadelphia Airport when flying between Chicago and Rehoboth Beach.
  • The cheapest flight from Chicago to Rehoboth Beach was found 78 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, February and March. The cheapest month to fly is October.
See more tips

Top 5 airlines serving Chicago to Rehoboth Beach

 
Need help choosing which airline to fly with from Chicago to Rehoboth Beach? 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
DeltaOverall score based on 10561 reviews
7.4Food
8.0Entertainment
8.2Boarding
8.6Crew
7.9Comfort
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

When we landed, they kept us on the plane for almost 25 minutes. Could do better.

worst trip ever Spirit lost our Baggs which were never put on the plane in Atlanta. 24 hours ago they are telling me now that the bags are still missing.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Book cheap flights from Chicago to Rehoboth Beach

Recent round-trip flight deals

6/5Wed
nonstopFrontier
2h 01mMDW-PHL
6/12Wed
nonstopFrontier
2h 11mPHL-MDW
$57
6/4Tue
nonstopFrontier
2h 03mORD-PHL
6/5Wed
nonstopFrontier
2h 21mPHL-ORD
$58
6/18Tue
nonstopFrontier
2h 02mMDW-PHL
6/25Tue
nonstopFrontier
2h 12mPHL-MDW
$60
6/5Wed
1 stop
13h 20mORD-PHL
6/8Sat
nonstop
2h 21mPHL-ORD
$73
6/11Tue
1 stop
6h 28mORD-PHL
6/18Tue
nonstop
2h 21mPHL-ORD
$79
6/7Fri
2 stopsSpirit Airlines
24h 52mORD-PHL
6/11Tue
1 stopSpirit Airlines
13h 35mPHL-ORD
$123
6/11Tue
2 stopsSpirit Airlines
14h 27mORD-PHL
6/12Wed
1 stopSpirit Airlines
11h 18mPHL-ORD
$124
6/7Fri
1 stopDelta
4h 14mORD-PHL
6/8Sat
1 stopDelta
5h 20mPHL-ORD
$188
7/12Fri
1 stopDelta
5h 10mORD-PHL
7/14Sun
1 stopDelta
3h 55mPHL-ORD
$200
6/20Thu
nonstopAmerican Airlines
2h 04mORD-PHL
6/21Fri
1 stopAmerican Airlines
3h 47mPHL-ORD
$204

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Recent one-way flight deals

5/29Wed
nonstopFrontier
2h 03mORD-PHL
$33
6/4Tue
1 stopSpirit Airlines
13h 20mORD-PHL
$34
6/19Wed
1 stopSun Country Air
14h 11mORD-PHL
$54
8/26Mon
nonstopAmerican Airlines
1h 57mORD-PHL
$66
6/1Sat
nonstopAmerican Airlines
2h 04mORD-PHL
$67
6/3Mon
1 stopSun Country Air
15h 46mORD-PHL
$69
5/29Wed
1 stopDelta
4h 41mMDW-PHL
$88
6/22Sat
1 stopDelta
6h 11mORD-PHL
$88
6/3Mon
nonstopUnited Airlines
2h 08mORD-PHL
$126
5/29Wed
nonstopUnited Airlines
2h 09mORD-PHL
$201

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Last minute flights from Chicago to Rehoboth Beach

Last minute flight, train and bus deals

5/28Tue
nonstopFrontier
2h 03mMDW-PHL
5/30Thu
nonstopFrontier
2h 16mPHL-MDW
$113
5/28Tue
nonstopFrontier
2h 03mMDW-PHL
5/29Wed
nonstopFrontier
2h 13mPHL-MDW
$114
5/25Sat
nonstopAmerican Airlines
1h 57mORD-PHL
5/28Tue
nonstopAmerican Airlines
2h 23mPHL-ORD
$201
5/27Mon
multi-stopAmerican Airlines
4h 21mORD-PHL
5/30Thu
nonstopAmerican Airlines
2h 23mPHL-ORD
$209
5/28Tue
multi-stopDelta
4h 17mMDW-PHL
5/29Wed
multi-stopDelta
4h 06mPHL-MDW
$233
5/25Sat
multi-stopDelta
7h 17mORD-PHL
6/1Sat
multi-stopDelta
6h 25mPHL-ORD
$233
5/27Mon
nonstopUnited Airlines
2h 08mORD-PHL
6/3Mon
multi-stopUnited Airlines
4h 35mPHL-ORD
$263
5/23Thu
multi-stopSpirit Airlines
13h 35mORD-PHL
5/29Wed
multi-stopSpirit Airlines
23h 26mPHL-ORD
$422
5/25Sat
multi-stopSpirit Airlines
20h 50mORD-PHL
5/28Tue
multi-stopSpirit Airlines
25h 14mPHL-ORD
$424
5/25Sat
multi-stopUnited Airlines
5h 42mORD-PHL
6/1Sat
multi-stopUnited Airlines
15h 01mPHL-ORD
$469

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Flights to Rehoboth Beach