Rehoboth Beach

$77+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Jul 30 — Aug 61
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Cheapflights Tip: The best prices from Chicago to Rehoboth Beach are usually found in September or August, booked 85 days in advance, depart on a Thursday or Friday and return on a Friday

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 July 25, 2025.

Round-trip from

$147
(FlightHub)

One-way from

$77
(Frontier)

Popular in

March

Cheapest in

September

Average price

$195
From Chicago (CHI) to Rehoboth Beach
One-way flight from Chicago (CHI) to Rehoboth Beach
Highest demand for flights based on searches. 26% potential increase in price ($86 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 July 25, 2025.

This FlightHub deal was found by Cheapflights users on 7/23. 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.
Fri 8/292:05 pmMDW - PHL
Nonstop2h 10mFrontier
Mon 9/112:00 pmPHL - MDW
Nonstop2h 10mFrontier
Deal found 7/23$147
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:20 amORD - PHL
Nonstop2h 06mFrontier
Sun 11/1610:21 amPHL - ORD
Nonstop2h 31mFrontier
Deal found 7/21$147
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:56 amORD - PHL
1 stop6h 42mMultiple Airlines
Mon 9/810:21 amPHL - ORD
Nonstop2h 37mMultiple Airlines
Deal found 7/24$151
This Southwest deal was found by Cheapflights users on 7/23. 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.
Wed 8/207:00 amMDW - PHL
Nonstop1h 55mSouthwest
Wed 8/2710:30 amPHL - MDW
Nonstop2h 10mSouthwest
Deal found 7/23$157
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Wed 8/208:50 amORD - PHL
Nonstop2h 11mUnited Airlines
Wed 8/2710:10 amPHL - ORD
Nonstop2h 22mUnited Airlines
Deal found 7/23$157
This FlightHub deal was found by Cheapflights users on 7/23. 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 8/138:12 pmORD - PHL
1 stop12h 44mSpirit Airlines
Wed 8/204:58 pmPHL - ORD
1 stop8h 01mSpirit Airlines
Deal found 7/23$160
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/175:00 amORD - PHL
Nonstop2h 03mAmerican Airlines
Wed 8/209:15 pmPHL - ORD
Nonstop2h 34mAmerican Airlines
Deal found 7/22$187
This Delta deal was found by Cheapflights users on 7/24. 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.
Sat 8/2310:31 amMDW - PHL
1 stop6h 05mDelta
Fri 9/125:15 pmPHL - MDW
1 stop5h 21mDelta
Deal found 7/24$197

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 July 25, 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

Fri 8/29

2:05 pm-5:15 pm

Nonstop2h 10m

Philadelphia

Mon 9/1

12:00 pm-1:10 pm

Nonstop2h 10m

$147

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 11/14

6:20 am-9:26 am

Nonstop2h 06m

Philadelphia

Sun 11/16

10:21 am-11:52 am

Nonstop2h 31m

$147

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 8/27

6:56 am-2:38 pm

1 stop6h 42m

Philadelphia

Mon 9/8

10:21 am-11:58 am

Nonstop2h 37m

$151

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 8/20

7:00 am-9:55 am

Nonstop1h 55m

Philadelphia

Wed 8/27

10:30 am-11:40 am

Nonstop2h 10m

$157

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 8/20

8:50 am-12:01 pm

Nonstop2h 11m

Philadelphia

Wed 8/27

10:10 am-11:32 am

Nonstop2h 22m

$157

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 8/13

8:12 pm-9:56 am

1 stop12h 44m

Philadelphia

Wed 8/20

4:58 pm-11:59 pm

1 stop8h 01m

$160

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sun 8/17

5:00 am-8:03 am

Nonstop2h 03m

Philadelphia

Wed 8/20

9:15 pm-10:49 pm

Nonstop2h 34m

$187

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 8/23

10:31 am-5:36 pm

1 stop6h 05m

Philadelphia

Tue 9/9

5:25 am-9:34 am

1 stop5h 09m

$197

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 8/23

1:30 pm-7:54 pm

1 stop5h 24m

Philadelphia

Fri 9/12

7:29 pm-11:52 pm

1 stop5h 23m

$197

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 8/15

6:40 pm-9:45 pm

Nonstop2h 05m

$77

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 20 results
1
2

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 July 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 85 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 July 25, 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 July 25, 2025.

The most flights from CHI to R3H are scheduled on a Thursday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).

How much does it cost to fly round-trip from Chicago to Rehoboth Beach?

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 July 25, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago to Rehoboth Beach to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Comfort

8.0

Food

7.0

Entertainment

7.6

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Comfort

8.0

Food

7.0

Entertainment

7.6

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very good

Comfort

8.0

Food

7.0

Entertainment

7.6

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Comfort

8.0

Food

7.0

Entertainment

7.6

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Comfort

8.0

Food

7.0

Entertainment

7.6

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Comfort

8.0

Food

7.0

Entertainment

7.6

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $77. Southwest flights start at $79 while deals on United Airlines start at $79 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 Air Canada (79%), United Airlines (74%) and Air New Zealand (68%).

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

    The cheapest flight price from Chicago to Rehoboth Beach is $70. On average you can expect to pay $1,219. The most popular route, (Chicago O'Hare Intl - Philadelphia), can usually be booked for $124.

  • 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

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Top 5 airlines flying from Chicago to Rehoboth Beach

Discover the top 5 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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$42Average$259FlexibilityNo cancel feeOn-time65%
FrontierCheapest$57Average$158FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$129Average$326FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$139Average$309FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$140Average$279FlexibilityNo cancel feeOn-time63%

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