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Rehoboth Beach

$69+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Rehoboth Beach are usually found in October or September, 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 September 16, 2025.

Round-trip from

$115
(Booking.com)

One-way from

$69
(Cheapflightsfares)

Popular in

March

Cheapest in

October

Average price

$185
From Chicago (CHI) to Rehoboth Beach
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One-way flight from Chicago (CHI) to Rehoboth Beach
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Highest demand for flights based on searches. 21% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 16, 2025.

This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/125:50 amORD - PHL
1 stop29h 12mFrontier
Sat 10/187:10 pmPHL - ORD
Nonstop2h 38mFrontier
Deal found 9/15$115
This Frontier deal was found by Cheapflights users on 9/15. 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.
Mon 9/296:10 amORD - PHL
Nonstop2h 15mFrontier
Mon 9/2912:30 pmPHL - ORD
1 stop8h 14mFrontier
Deal found 9/15$117
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:05 amMDW - PHL
1 stop7h 30mFrontier
Sun 10/266:10 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/15$120
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/318:26 amORD - PHL
Nonstop2h 13mFrontier
Sun 11/29:23 amPHL - ORD
Nonstop2h 29mFrontier
Deal found 9/14$120
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:14 pmMDW - PHL
Nonstop2h 00mFrontier
Sun 11/97:00 amPHL - MDW
Nonstop2h 13mFrontier
Deal found 9/16$121
This Frontier deal was found by Cheapflights users on 9/14. 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 10/1711:50 amORD - PHL
Nonstop2h 09mFrontier
Fri 10/175:12 pmPHL - ORD
1 stop9h 19mFrontier
Deal found 9/14$121
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:12 amMDW - PHL
1 stop7h 18mFrontier
Sun 11/25:15 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/15$122
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 11/145:11 amORD - PHL
1 stop5h 18mFrontier
Mon 11/176:00 amPHL - ORD
Nonstop2h 26mFrontier
Deal found 9/14$122
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:15 amMDW - PHL
Nonstop2h 01mFrontier
Sun 10/56:00 amPHL - MDW
Nonstop2h 11mFrontier
Deal found 9/14$123
This Frontier deal was found by Cheapflights users on 9/14. 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 10/1711:50 amORD - PHL
Nonstop2h 09mFrontier
Wed 10/2210:49 amPHL - ORD
1 stop6h 51mFrontier
Deal found 9/14$123
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/1012:13 pmMDW - PHL
Nonstop2h 00mFrontier
Mon 10/134:13 pmPHL - MDW
Nonstop2h 14mFrontier
Deal found 9/14$124
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:50 pmORD - PHL
Nonstop2h 20mFrontier
Wed 10/295:00 pmPHL - ORD
1 stop21h 59mFrontier
Deal found 9/14$124

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 September 16, 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

Tue 10/14

6:45 am-9:40 am

Nonstop1h 55m

Philadelphia

Sat 10/18

12:05 pm-1:10 pm

Nonstop2h 05m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 12/10

2:30 pm-5:39 pm

Nonstop2h 09m

Philadelphia

Sat 12/13

5:07 pm-6:36 pm

Nonstop2h 29m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/25

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

Tue 10/28

5:25 am-6:30 am

Nonstop2h 05m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 11/1

6:13 pm-9:21 pm

Nonstop2h 08m

Philadelphia

Tue 11/11

5:07 pm-6:35 pm

Nonstop2h 28m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 11/1

12:50 pm-3:40 pm

Nonstop1h 50m

Philadelphia

Tue 11/11

6:00 am-7:15 am

Nonstop2h 15m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 10/18

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

Tue 10/21

6:05 pm-7:10 pm

Nonstop2h 05m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 9/29

8:15 am-11:16 am

Nonstop2h 01m

Philadelphia

Wed 10/8

9:14 pm-9:47 am

1 stop13h 33m

$147

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 10/17

9:15 pm-12:10 am

Nonstop1h 55m

Philadelphia

Tue 10/21

6:05 pm-7:10 pm

Nonstop2h 05m

$158

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 10/11

8:45 am-11:56 am

Nonstop2h 11m

Philadelphia

Tue 10/14

6:30 am-7:52 am

Nonstop2h 22m

$159

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 10/14

2:50 pm-5:45 pm

Nonstop1h 55m

Philadelphia

Wed 10/15

5:25 am-6:30 am

Nonstop2h 05m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 43 results
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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 September 12, 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 September 16, 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 Thursday evenings 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 September 16, 2025.

The most flights from CHI to R3H are scheduled on a Monday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 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 September 16, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Rehoboth Beach?

    Airlines like Southwest, United Airlines, and Frontier fly from Chicago to Rehoboth Beach in about 1h 55m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 666 mi. All flights are typically nonstop.

  • 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 United Airlines (80%), Air Canada (77%) and Copa Airlines (72%).

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

    The cheapest flight price from Chicago to Rehoboth Beach is $65. On average you can expect to pay $218. The most popular route, (Chicago O'Hare Intl - Philadelphia), can usually be booked for $125.

  • 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 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$226FlexibilityNo cancel feeOn-time65%
FrontierCheapest$64Average$162FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$477FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$124Average$318FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$153Average$284FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$154Average$313FlexibilityNo cancel feeOn-time69%

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