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Rehoboth Beach

$60+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Rehoboth Beach are usually found in October 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 November 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$107
(CheapOair)

One-way from

$60
(Travelocity)

Popular in

March

Cheapest in

October

Average price

$256
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
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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. 16% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 26, 2025.

This CheapOair deal was found by Cheapflights users on 11/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:26 pmORD - PHL
1 stop6h 50mSpirit Airlines
Mon 12/1510:22 amPHL - ORD
1 stop9h 14mSpirit Airlines
Deal found 11/26$107
This Frontier deal was found by Cheapflights users on 11/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/122:00 pmORD - PHL
Nonstop2h 15mFrontier
Sun 1/1112:42 pmPHL - ORD
Nonstop2h 40mFrontier
Deal found 11/24$108
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/178:00 amORD - PHL
1 stop7h 52mFrontier
Tue 1/134:45 pmPHL - ORD
Nonstop2h 40mFrontier
Deal found 11/24$109
This Frontier deal was found by Cheapflights users on 11/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:11 amORD - PHL
1 stop12h 19mFrontier
Mon 1/1212:42 pmPHL - ORD
Nonstop2h 40mFrontier
Deal found 11/24$110
This Priceline deal was found by Cheapflights users on 11/25. 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.
Mon 12/83:23 pmORD - PHL
Nonstop2h 15mMultiple Airlines
Wed 12/104:00 pmPHL - ORD
1 stop9h 09mMultiple Airlines
Deal found 11/25$111
This CheapOair deal was found by Cheapflights users on 11/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/178:00 amORD - PHL
1 stop7h 52mFrontier
Sun 1/1112:42 pmPHL - ORD
Nonstop2h 40mFrontier
Deal found 11/25$114
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Tue 12/163:26 pmORD - PHL
1 stop6h 50mMultiple Airlines
Fri 1/91:59 pmPHL - ORD
Nonstop2h 40mMultiple Airlines
Deal found 11/24$115
This Priceline deal was found by Cheapflights users on 11/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:26 pmORD - PHL
1 stop6h 50mSpirit Airlines
Sun 12/1410:22 amPHL - ORD
1 stop9h 14mSpirit Airlines
Deal found 11/24$116
This Priceline deal was found by Cheapflights users on 11/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:00 amORD - PHL
1 stop8h 44mMultiple Airlines
Fri 12/1211:10 amPHL - ORD
Nonstop2h 30mMultiple Airlines
Deal found 11/24$117
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Fri 12/195:15 amORD - PHL
Nonstop2h 15mFrontier
Tue 1/134:45 pmPHL - ORD
Nonstop2h 40mFrontier
Deal found 11/24$118
This Frontier deal was found by Cheapflights users on 11/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:15 pmORD - PHL
Nonstop2h 15mFrontier
Tue 12/3010:00 amPHL - ORD
1 stop8h 51mFrontier
Deal found 11/24$120
This Southwest deal was found by Cheapflights users on 11/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:05 amMDW - PHL
Nonstop1h 55mSouthwest
Tue 1/275:40 amPHL - MDW
Nonstop2h 20mSouthwest
Deal found 11/24$139

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 November 26, 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

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 1/8

8:27 pm-8:09 pm

1 stop22h 42m

Philadelphia

Mon 1/12

12:42 pm-2:22 pm

Nonstop2h 40m

$111

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 12/24

2:25 pm-5:28 pm

Nonstop2h 03m

Philadelphia

Wed 12/31

8:27 am-9:55 am

Nonstop2h 28m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 12/25

9:29 pm-12:45 am

Nonstop2h 16m

Philadelphia

Thu 1/1

8:27 am-9:55 am

Nonstop2h 28m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 1/7

2:15 pm-5:05 pm

Nonstop1h 50m

Philadelphia

Mon 1/12

12:15 pm-1:30 pm

Nonstop2h 15m

$148

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 1/16

8:56 am-12:07 pm

Nonstop2h 11m

Philadelphia

Tue 1/20

6:30 am-7:59 am

Nonstop2h 29m

$148

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 12/24

2:15 pm-5:30 pm

Nonstop2h 15m

Philadelphia

Mon 12/29

10:00 am-9:02 am

1 stop24h 02m

$150

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 2/6

2:30 pm-5:34 pm

Nonstop2h 04m

Philadelphia

Sun 2/8

5:00 pm-6:30 pm

Nonstop2h 30m

$167

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 1/9

12:44 pm-7:48 pm

1 stop6h 04m

Philadelphia

Mon 1/12

9:52 am-6:39 pm

1 stop9h 47m

$171

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 12/26

5:15 am-8:30 am

Nonstop2h 15m

Philadelphia

Thu 1/1

6:30 am-10:40 am

1 stop5h 10m

$176

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 12/24

6:08 pm-11:17 pm

1 stop4h 09m

Philadelphia

Wed 12/31

11:40 am-5:19 pm

1 stop6h 39m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 42 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 November 21, 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, February is the cheapest month in which you can book a flight from Chicago to Rehoboth Beach (average of $57). Flying from Chicago to Rehoboth Beach in January is currently the most expensive (average of $112). 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 November 26, 2025.

It’s typically best to fly out from Chicago to Rehoboth Beach in the evening. Doing so could potentially save you 28% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 Monday 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 November 26, 2025.

The most flights from CHI to R3H are scheduled on a Monday (51 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 November 26, 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
4,254 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
9,046 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
11,038 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
8,158 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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
3,099 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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 Frontier, United Airlines, and Southwest fly from Chicago to Rehoboth Beach in about 1h 50m. The time it takes to get you to your destination can typically vary by up to 20h 52m. Airlines will cover a distance of 666 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $60. Southwest flights start at $70 while deals on United Airlines start at $70 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 New Zealand (82%), Air Canada (79%) and United Airlines (78%).

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

    The cheapest flight price from Chicago to Rehoboth Beach is $55. On average you can expect to pay $280. The most popular route, (Chicago O'Hare Intl - Philadelphia), can usually be booked for $96.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Rehoboth Beach (average of $57). Flying from Chicago to Rehoboth Beach in January is currently the most expensive (average of $112). 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$225FlexibilityNo cancel feeOn-time65%
FrontierCheapest$62Average$162FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$477FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$143Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$148Average$317FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$289FlexibilityNo cancel feeOn-time63%

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