$99 Find Cheap Flights from Chicago to Rehoboth Beach - Compare and Save

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 8/3. 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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Everything you should know

Cheapest round-trip
$183
Typical prices: $180-$325
Frontier
Wed 9/23Mon 9/28
ORD - PHL • 2 stops
Cheapest non-stop
$187
Typical prices: $183-$353
Frontier
Mon 8/10Sat 8/15
ORD - PHL • Non-stop
Arrival airport
You can't fly directly to Rehoboth Beach. It is served by Philadelphia (PHL), located 80.4 miles from Rehoboth Beach.
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Flight Deals
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Flight Deals

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

Wed, Sep 23 - Mon, Sep 28
Frontier Logo
2:46 pm - 7:36 am
ORD
-
PHL
15h 50m
2 stops
Frontier Logo
11:05 am - 12:41 pm
PHL
-
ORD
2h 36mnonstop
$183Frontier
Sat, Sep 5 - Mon, Sep 7
Frontier Logo
1:59 pm - 10:33 pm
ORD
-
PHL
7h 34m
1 stop
Frontier Logo
6:00 am - 7:29 am
PHL
-
ORD
2h 29mnonstop
$184Frontier
Wed, Sep 16 - Mon, Sep 21
Frontier Logo
2:46 pm - 7:36 am
ORD
-
PHL
15h 50m
2 stops
Frontier Logo
11:05 am - 12:41 pm
PHL
-
ORD
2h 36mnonstop
$185Frontier
Fri, Aug 14 - Mon, Aug 17
Frontier Logo
8:58 pm - 12:21 am
ORD
-
PHL
2h 23mnonstop
Frontier Logo
1:32 pm - 7:53 pm
PHL
-
ORD
7h 21m
1 stop
$186Frontier
Thu, Oct 1 - Sun, Oct 4
Frontier Logo
6:50 am - 10:00 am
ORD
-
PHL
2h 10mnonstop
Frontier Logo
7:10 am - 12:02 pm
PHL
-
ORD
5h 52m
1 stop
$187Frontier
Thu, Oct 1 - Sun, Oct 4
Frontier Logo
6:50 am - 10:00 am
ORD
-
PHL
2h 10mnonstop
Frontier Logo
7:10 am - 12:02 pm
PHL
-
ORD
5h 52m
1 stop
$188Frontier
Tue, Aug 25 - Wed, Sep 2
Frontier Logo
1:59 pm - 10:33 pm
ORD
-
PHL
7h 34m
1 stop
Frontier Logo
8:30 am - 8:08 pm
PHL
-
ORD
12h 38m
1 stop
$189Frontier
Thu, Oct 15 - Sat, Oct 17
Frontier Logo
7:29 pm - 10:47 pm
ORD
-
PHL
2h 18mnonstop
Frontier Logo
12:43 pm - 8:28 pm
PHL
-
ORD
8h 45m
1 stop
$190Frontier
Wed, Nov 4 - Wed, Nov 11
Frontier Logo
6:30 am - 1:12 pm
ORD
-
PHL
5h 42m
1 stop
Frontier Logo
7:10 am - 12:02 pm
PHL
-
ORD
5h 52m
1 stop
$191Frontier
Thu, Aug 6 - Mon, Aug 17
Frontier Logo
8:52 pm - 12:15 am
ORD
-
PHL
2h 23mnonstop
Frontier Logo
6:11 pm - 7:53 pm
PHL
-
ORD
2h 42mnonstop
$192Frontier
Useful Info

Good to know

Low season

February

Cheapest flight

$99
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 18% increase in price.
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 55m.

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

    78 direct flights run between Chicago and Rehoboth Beach on a daily basis. On average, there are about 549 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 Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

  • 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 5 days, the cheapest one-way ticket between Chicago and Rehoboth Beach found on KAYAK was with Frontier for $45. Frontier offered a round-trip connection from $67 and American Airlines from $157.

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 80 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 May, June and July. The cheapest month to fly is October.

Reviews of the top 4 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 4236 reviews
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

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

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight from Chicago to Rehoboth Beach

Complete your trip to Rehoboth Beach with a hotel stay or car rental