$58 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 1/12. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$105
Overall average: $344
United Airlines
Thu 2/5Sat 2/7
ORD - PHL • Non-stop
Cheapest one-way
$58
Typical prices: $109-$174
Frontier
Mon 1/12
MDW - PHL • 1 stop
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Flight Deals
Useful Info
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

Thu, Feb 5 - Sat, Feb 7
United Airlines Logo
8:56 am - 12:07 pm
ORD
-
PHL
2h 11mnonstop
United Airlines Logo
5:00 pm - 6:30 pm
PHL
-
ORD
2h 30mnonstop
$105United Airlines
Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
5:26 pm - 8:25 pm
ORD
-
PHL
1h 59mnonstop
American Airlines Logo
4:50 pm - 6:34 pm
PHL
-
ORD
2h 44mnonstop
$106American Airlines
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
7:35 pm - 10:50 pm
ORD
-
PHL
2h 15mnonstop
Multiple Airlines Logo
8:34 pm - 8:18 am
PHL
-
ORD
12h 44m1 stop
$108Multiple Airlines
Tue, Jan 20 - Thu, Jan 22
United Airlines Logo
6:20 pm - 9:36 pm
ORD
-
PHL
2h 16mnonstop
United Airlines Logo
10:10 am - 11:38 am
PHL
-
ORD
2h 28mnonstop
$109United Airlines
Wed, Jan 7 - Thu, Jan 15
Frontier Logo
4:49 pm - 12:51 am
ORD
-
PHL
7h 02m1 stop
Frontier Logo
4:45 pm - 6:25 pm
PHL
-
ORD
2h 40mnonstop
$110Frontier
Fri, Feb 20 - Sat, Feb 28
Frontier Logo
3:15 pm - 6:26 pm
ORD
-
PHL
2h 11mnonstop
Frontier Logo
8:04 am - 2:20 pm
PHL
-
ORD
7h 16m1 stop
$111Frontier
Wed, Dec 31 - Mon, Jan 12
Multiple Airlines Logo
2:15 pm - 5:30 pm
ORD
-
PHL
2h 15mnonstop
Multiple Airlines Logo
8:20 am - 9:03 pm
PHL
-
ORD
13h 43m1 stop
$114Multiple Airlines
Fri, Jan 30 - Mon, Feb 2
Spirit Airlines Logo
8:43 pm - 8:47 am
ORD
-
PHL
11h 04m1 stop
Spirit Airlines Logo
8:20 am - 7:38 pm
PHL
-
ORD
12h 18m1 stop
$115Spirit Airlines
Wed, Jan 21 - Wed, Jan 28
Southwest Logo
5:30 pm - 8:20 pm
MDW
-
PHL
1h 50mnonstop
Southwest Logo
5:45 pm - 7:00 pm
PHL
-
MDW
2h 15mnonstop
$125Southwest
Fri, Jan 30 - Wed, Feb 4
Southwest Logo
5:30 pm - 8:20 pm
MDW
-
PHL
1h 50mnonstop
Southwest Logo
5:45 pm - 7:00 pm
PHL
-
MDW
2h 15mnonstop
$137Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$58
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 3% 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 50m.

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

    76 direct flights run between Chicago and Rehoboth Beach on a daily basis. On average, there are about 532 departures each week.

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

    Consider leaving on a Thursday 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 Sundays.

  • 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 $49. Spirit Airlines offered a round-trip connection from $63 and Frontier from $72.

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 October.

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 4251 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025
BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

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.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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.

Everything was smoothly and convenient! Just stay in this way!

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Terrible Airline I will never fly that airline again. Shame on you for recommending them.

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

I didn't eat, so I can't rate the food. Delayed set off was beyond

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

I hope you continue to be one of the great company

Crew are always very angry and dismissive like they seem they are being forced to work. In addition, there was a long line for the bathrooms, and only one was allowed to be used. No reason was given for only one bathroom being available; apparently, the stewardess was more interested in using the jumpseat instead of allowing the customers to use the bathroom.

Very positive in both directions. Safe travels, nice staff, lost and found in fact found my phone under my chair! I was out of cash after my NYC trip otherwise I would've offered a reward for helping my day out immensly! Thanks you so much Spirit staff!

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

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

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

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

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