$70 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 2/18. 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

KAYAK searches hundreds of travel sites at once for deals on flights from Chicago to Rehoboth Beach

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$125
Overall average: $356
Multiple Airlines
Thu 3/12Mon 3/16
ORD - PHL • Non-stop
Cheapest non-stop
$129
Typical prices: $274-$463
Frontier
Mon 2/23Mon 3/2
ORD - PHL • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Rehoboth Beach!
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, Mar 12 - Mon, Mar 16
Multiple Airlines Logo
3:21 pm - 6:30 pm
ORD
-
PHL
2h 09mnonstop
Multiple Airlines Logo
8:18 am - 6:21 pm
PHL
-
ORD
11h 03m
1 stop
$125Multiple Airlines
Sun, Apr 5 - Wed, Apr 8
Multiple Airlines Logo
6:00 am - 9:14 am
ORD
-
PHL
2h 14mnonstop
Multiple Airlines Logo
8:18 am - 6:21 pm
PHL
-
ORD
11h 03m
1 stop
$126Multiple Airlines
Mon, Feb 23 - Tue, Feb 24
Frontier Logo
10:15 am - 1:24 pm
ORD
-
PHL
2h 09mnonstop
Frontier Logo
11:40 am - 4:52 pm
PHL
-
ORD
6h 12m
1 stop
$127Frontier
Sat, Feb 28 - Tue, Mar 3
Frontier Logo
6:25 am - 6:11 pm
MDW
-
PHL
10h 46m
1 stop
Frontier Logo
11:40 am - 7:07 pm
PHL
-
MDW
8h 27m
1 stop
$128Frontier
Sat, Feb 28 - Wed, Mar 4
Frontier Logo
12:06 pm - 12:21 am
ORD
-
PHL
11h 15m
1 stop
Frontier Logo
11:40 am - 4:52 pm
PHL
-
ORD
6h 12m
1 stop
$128Frontier
Mon, Feb 23 - Mon, Mar 2
Frontier Logo
10:15 am - 1:24 pm
ORD
-
PHL
2h 09mnonstop
Frontier Logo
7:35 am - 9:11 am
PHL
-
ORD
2h 36mnonstop
$129Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
3:40 pm - 12:44 am
ORD
-
PHL
8h 04m
1 stop
Frontier Logo
12:38 pm - 10:39 pm
PHL
-
ORD
11h 01m
1 stop
$130Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
3:40 pm - 12:44 am
ORD
-
PHL
8h 04m
1 stop
Frontier Logo
7:35 am - 9:11 am
PHL
-
ORD
2h 36mnonstop
$131Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
3:40 pm - 10:39 pm
ORD
-
PHL
29h 59m
1 stop
Frontier Logo
7:18 pm - 10:51 am
PHL
-
ORD
16h 33m
1 stop
$132Frontier
Mon, Feb 23 - Mon, Mar 2
Frontier Logo
4:42 pm - 1:01 am
ORD
-
PHL
7h 19m
1 stop
Frontier Logo
12:38 pm - 10:39 pm
PHL
-
ORD
11h 01m
1 stop
$133Frontier
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$70
Best time to beat the crowds but there is an average 16% increase in price.
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?

    60 direct flights run between Chicago and Rehoboth Beach on a daily basis. On average, there are about 423 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 Saturdays 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 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 $67.

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 4268 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Great flight but super high price. Glad it was a business trip and not personal

10.0 ExcellentPieter, Jan 2026
LGB - DAL
Read more Southwest reviews

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

Horribly late because they had no crew!!! And then jet bridge didn’t work!! Then we arrived at a gate at lax miles away that we had to take a shuttle to a terminal!! I was over 3 hours late to getting the LA! Should have been here at 8:30 and at an appointment at 10:30 and arrived and left lax at 11 am!! Horrible experience!!!

Extra legroom with my upgrade bundle. Clean aircraft, on-time departure, early arrival. Good value for the price.

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Even though the plane was delayed from the previous airport, the staff recognized this and kept us informed. The flight crew was absolutely awesome from on my flight from Ft. Meyers to AC. Great experience all around!

Flight was delayed would have liked it to have been on time. I didn't experience the food or entertainment but the boarding process was smooth and the flight crew worked well together and did a great job!

Not seat assigned because overbooking. We could go because some people decided to give their seats.

Spirit loves to pick and choose when to harass you about your personal item. I’ve flown numerous times with the same bag with no problem yet flying out of Orlando they forced me to pay $99 for a carry on and then ran out of overhead space. Do better!

For the price of the fare, there really isn’t much to complain about.

didn't order food on board. there's no way to hold a water botton on the way. otherwise it was a pleasant flight, thanks to the crew.

Even though there was a delay the crew was exceptional.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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