$68 Find Cheap Flights from Chicago to Rehoboth Beach

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 10/6. 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.
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Cheap Flights from Chicago to Rehoboth Beach (CHI-PHL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Rehoboth Beach that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Rehoboth Beach

Fri, Sep 19 - Sun, Sep 21
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
Frontier Logo
6:00 am - 7:11 amPHL-MDW
2h 11mnonstop
$125Frontier
Find Deal
Sat, Sep 6 - Sun, Sep 7
Frontier Logo
8:00 am - 7:31 amORD-PHL
22h 31m1 stop
Frontier Logo
10:21 am - 11:58 amPHL-ORD
2h 37mnonstop
$125Frontier
Find Deal
Thu, Sep 25 - Sat, Sep 27
Frontier Logo
8:15 am - 11:16 amMDW-PHL
2h 01mnonstop
Frontier Logo
6:37 pm - 11:17 pmPHL-MDW
5h 40m1 stop
$126Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
6:10 am - 9:25 amORD-PHL
2h 15mnonstop
Frontier Logo
6:15 am - 4:51 pmPHL-ORD
11h 36m1 stop
$126Frontier
Find Deal
Sat, Oct 4 - Sat, Oct 11
Southwest Logo
5:35 pm - 8:30 pmMDW-PHL
1h 55mnonstop
Southwest Logo
5:10 pm - 6:15 pmPHL-MDW
2h 05mnonstop
$139Southwest
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Wed, Sep 24 - Sat, Sep 27
United Airlines Logo
8:45 am - 11:56 amORD-PHL
2h 11mnonstop
United Airlines Logo
6:30 am - 7:52 amPHL-ORD
2h 22mnonstop
$139United Airlines
Find Deal
Sat, Oct 4 - Sun, Oct 12
Southwest Logo
5:35 pm - 8:30 pmMDW-PHL
1h 55mnonstop
Southwest Logo
6:00 am - 7:05 amPHL-MDW
2h 05mnonstop
$158Southwest
Find Deal
Sat, Oct 4 - Mon, Oct 6
United Airlines Logo
7:30 am - 10:39 amORD-PHL
2h 09mnonstop
United Airlines Logo
6:30 am - 7:52 amPHL-ORD
2h 22mnonstop
$158United Airlines
Find Deal
Tue, Sep 9 - Fri, Sep 12
 Logo
11:57 am - 11:47 pmORD-PHL
10h 50m1 stop
 Logo
5:15 am - 10:31 amPHL-ORD
6h 16m1 stop
Tue, Sep 16 - Fri, Sep 19
 Logo
11:57 am - 11:47 pmORD-PHL
10h 50m1 stop
 Logo
10:16 pm - 3:17 pmPHL-ORD
18h 01m1 stop
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 20% lower on average.
Flight from Chicago Midway 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 55m.

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

    60 direct flights run between Chicago and Rehoboth Beach on a daily basis. On average, there are about 426 departures each week.

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

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

  • 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 $68. Frontier offered a round-trip connection from $125 and Southwest from $139.

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 85 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is September.

Reviews of the 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
SouthwestOverall score based on 4242 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

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