HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Rehoboth Beach

$84+ Cheap flights from Chicago (CHI) to Rehoboth Beach, DE

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Rehoboth Beach with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Rehoboth Beach are usually found in August or September, booked 66 days in advance, depart on a Thursday or Friday and return on a Thursday

Cheap flight deals from Chicago to Rehoboth Beach

Keep the following information in mind while searching for Chicago to Rehoboth Beach flight deals. Data was last updated April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$161
(Southwest)

One-way from

$84
(FlightHub)

Popular in

March

Cheapest in

August

Average price

$268
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
Search Deals
From Chicago (CHI) to Rehoboth Beach
Search Deals
One-way flight from Chicago (CHI) to Rehoboth Beach
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($102 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Chicago to Rehoboth Beach

Cheapest flights from Chicago to Rehoboth Beach
Explore the most affordable flight options available from Chicago to Rehoboth Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:20 pmMDW - PHL
Nonstop1h 55mSouthwest
Sun 5/253:15 pmPHL - MDW
Nonstop2h 10mSouthwest
Deal found 4/23$161
This Cheapflightsfares deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/208:17 pmORD - PHL
Nonstop2h 27mFrontier
Sun 6/225:45 amPHL - ORD
Nonstop2h 32mFrontier
Deal found 4/23$161
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/259:36 pmORD - PHL
Nonstop2h 09mAmerican Airlines
Tue 7/14:23 pmPHL - ORD
Nonstop2h 32mAmerican Airlines
Deal found 4/23$169
This Flightnetwork deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:52 pmMDW - PHL
Nonstop2h 04mFrontier
Mon 6/96:35 pmPHL - MDW
Nonstop2h 17mFrontier
Deal found 4/23$170
This FlightHub deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1412:41 pmORD - PHL
1 stop9h 02mMultiple Airlines
Mon 5/195:01 pmPHL - ORD
Nonstop2h 28mMultiple Airlines
Deal found 4/23$181
This Mytrip deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:47 amORD - PHL
1 stop23h 01mSpirit Airlines
Mon 5/124:00 pmPHL - ORD
2 stops32h 04mSpirit Airlines
Deal found 4/22$205
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2911:15 amORD - PHL
Nonstop2h 09mUnited Airlines
Mon 6/28:31 amPHL - ORD
Nonstop2h 24mUnited Airlines
Deal found 4/23$217
This JetBlue deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/149:40 amORD - PHL
1 stop8h 00mJetBlue
Tue 6/1710:15 amPHL - ORD
1 stop6h 38mJetBlue
Deal found 4/23$226
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/61:45 pmORD - PHL
1 stop4h 29mDelta
Mon 6/164:05 pmPHL - ORD
1 stop6h 19mDelta
Deal found 4/23$237
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/166:25 pmMDW - PHL
1 stop3h 40mDelta
Sat 5/174:58 pmPHL - MDW
1 stop5h 16mDelta
Deal found 4/23$238
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:00 amORD - PHL
1 stop11h 10mSouthwest
Sat 5/317:15 amPHL - ORD
1 stop6h 50mSouthwest
Deal found 4/23$242
This Kissandfly.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/28:03 pmMDW - PHL
2 stops22h 44mMultiple Airlines
Sun 5/46:00 amPHL - MDW
1 stop3h 40mMultiple Airlines
Deal found 4/23$369

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Rehoboth Beach that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2025.
Use the filters below to find and compare flights from Chicago to Rehoboth Beach that are best for you.

Fly from

Chicago

Fly to

Rehoboth Beach

Route

Depart

Return

Price

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 5/24

6:20 pm-9:15 pm

Nonstop1h 55m

Philadelphia

Sun 5/25

3:15 pm-4:25 pm

Nonstop2h 10m

$161

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 6/20

8:17 pm-11:44 pm

Nonstop2h 27m

Philadelphia

Sun 6/22

5:45 am-7:17 am

Nonstop2h 32m

$161

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 6/25

9:36 pm-12:45 am

Nonstop2h 09m

Philadelphia

Tue 7/1

4:23 pm-5:55 pm

Nonstop2h 32m

$169

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 6/6

8:52 pm-11:56 pm

Nonstop2h 04m

Philadelphia

Mon 6/9

6:35 pm-7:52 pm

Nonstop2h 17m

$170

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 5/14

12:41 pm-10:43 pm

1 stop9h 02m

Philadelphia

Mon 5/19

5:01 pm-6:29 pm

Nonstop2h 28m

$181

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 5/10

7:47 am-7:48 am

1 stop23h 01m

Philadelphia

Mon 5/12

4:00 pm-11:04 pm

2 stops32h 04m

$205

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 5/29

11:15 am-2:24 pm

Nonstop2h 09m

Philadelphia

Mon 6/2

8:31 am-9:55 am

Nonstop2h 24m

$217

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 6/14

9:40 am-6:40 pm

1 stop8h 00m

Philadelphia

Tue 6/17

10:15 am-3:53 pm

1 stop6h 38m

$226

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 6/6

3:57 pm-10:55 pm

1 stop5h 58m

Philadelphia

Mon 6/9

5:30 am-10:09 am

1 stop5h 39m

$237

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 5/16

6:25 pm-11:05 pm

1 stop3h 40m

Philadelphia

Sat 5/17

4:58 pm-9:14 pm

1 stop5h 16m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 26 results
1
2
3

Best time to book a flight from Chicago to Rehoboth Beach

Have a flexible travel schedule? Discover the best time to fly to Rehoboth Beach from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Rehoboth Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Rehoboth Beach. Price data was last updated on April 18, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Rehoboth Beach, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Rehoboth Beach?

Currently, August is the cheapest month in which you can book a flight from Chicago to Rehoboth Beach (average of $236). Flying from Chicago to Rehoboth Beach in March is currently the most expensive (average of $295). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to R3H?

Find hourly flight availability from Chicago to Rehoboth Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Rehoboth Beach as you normally would.

What is the cheapest day to fly from Chicago to Rehoboth Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Rehoboth Beach. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Rehoboth Beach flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Rehoboth Beach

Explore weekly flight availability from Chicago to Rehoboth Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 24, 2025.

The most flights from CHI to R3H are scheduled on a Monday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Rehoboth Beach by month

Plan your trip to Rehoboth Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Rehoboth Beach ranges from 2.7 - 4.4 inches per month. July is typically the wettest month, when rainfall can reach 4.4 in. February is typically the driest time to visit Rehoboth Beach when rainfall is around 2.7 in.

Temperature in Rehoboth Beach by month

Plan your trip to Rehoboth Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Rehoboth Beach, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

Reviews of airlines servicing Rehoboth Beach

Get insights into the airlines that provide service to Rehoboth Beach. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Rehoboth Beach. Reviews last updated April 24, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Chicago to Rehoboth Beach. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Chicago to Rehoboth Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Rehoboth Beach one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $84. Spirit Airlines flights start at $85 while deals on American Airlines start at $89 one-way.

  • What are the most reliable airlines from Chicago to Rehoboth Beach?

    The top 3 most reliable airlines when flying from Chicago to Rehoboth Beach are Qatar Airways (86%), Alaska Airlines (82%) and Air Canada (81%).

  • What are the cheapest flights from Chicago to Rehoboth Beach?

    The cheapest flight price from Chicago to Rehoboth Beach is $85. On average you can expect to pay $956. The most popular route, (Chicago O'Hare Intl - Philadelphia), can usually be booked for $174.

  • Can I find deals for flights from Chicago to Rehoboth Beach that include hotel bookings?

    Yes. In addition to deals on Chicago to Rehoboth Beach flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Rehoboth Beach?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Rehoboth Beach.

  • Can I find deals for business class flights from Chicago to Rehoboth Beach?

    Yes. Cheapflights offers flight deals from Chicago to Rehoboth Beach by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Rehoboth Beach?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Rehoboth Beach (average of $236). Flying from Chicago to Rehoboth Beach in March is currently the most expensive (average of $295). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 6 airlines flying from Chicago to Rehoboth Beach

Discover the top 6 airlines that operate flights from Chicago to Rehoboth Beach. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$52Average$135FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$257FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$122Average$344FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$137Average$294FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$140Average$280FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$244FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.