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Rehoboth Beach

$70+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
feb. 13 — feb. 201
vie. 2/13
vie. 2/20
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Rehoboth Beach are usually found in October or January, booked 85 days in advance, depart on a Friday or Thursday 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 enero 14, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$97
(Booking.com)

One-way from

$70
(Expedia)

Popular in

March

Cheapest in

October

Average price

$209
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. 17% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 enero 14, 2026.

This Booking.com deal was found by Cheapflights users on 1/13. 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.
mié. 2/412:44 pm
ORD
-
PHL
1 stop6h 04m
Multiple Airlines
vie. 2/69:09 pm
PHL
-
ORD
Nonstop2h 40m
Multiple Airlines
Deal found 1/13$97
This Priceline deal was found by Cheapflights users on 1/11. 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.
vie. 2/64:44 pm
ORD
-
PHL
Nonstop2h 15m
Multiple Airlines
mar. 2/1012:40 pm
PHL
-
ORD
1 stop9h 23m
Multiple Airlines
Deal found 1/11$102
This Booking.com deal was found by Cheapflights users on 1/12. 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.
vie. 2/64:44 pm
ORD
-
PHL
Nonstop2h 15m
Multiple Airlines
mié. 2/1112:40 pm
PHL
-
ORD
1 stop9h 23m
Multiple Airlines
Deal found 1/12$105
This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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.
mié. 2/1110:48 am
ORD
-
PHL
1 stop8h 00m
Spirit Airlines
mié. 2/185:26 pm
PHL
-
ORD
1 stop7h 21m
Spirit Airlines
Deal found 1/14$107
This Frontier deal was found by Cheapflights users on 1/12. 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.
mié. 2/48:10 am
ORD
-
PHL
1 stop6h 27m
Frontier
vie. 2/69:09 pm
PHL
-
ORD
Nonstop2h 40m
Frontier
Deal found 1/12$108
This Booking.com deal was found by Cheapflights users on 1/12. 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.
jue. 3/123:21 pm
ORD
-
PHL
Nonstop2h 09m
Frontier
dom. 3/1512:45 pm
PHL
-
ORD
Nonstop2h 36m
Frontier
Deal found 1/12$109
This Booking.com deal was found by Cheapflights users on 1/13. 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.
mar. 1/2710:48 am
ORD
-
PHL
1 stop10h 15m
Multiple Airlines
vie. 1/309:09 pm
PHL
-
ORD
Nonstop2h 40m
Multiple Airlines
Deal found 1/13$114
This Super.com deal was found by Cheapflights users on 1/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/304:44 pm
ORD
-
PHL
Nonstop2h 15m
Frontier
lun. 2/27:47 pm
PHL
-
ORD
Nonstop2h 40m
Frontier
Deal found 1/12$116
This Super.com deal was found by Cheapflights users on 1/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/64:44 pm
ORD
-
PHL
Nonstop2h 15m
Frontier
lun. 2/97:47 pm
PHL
-
ORD
Nonstop2h 40m
Frontier
Deal found 1/12$118
This Expedia deal was found by Cheapflights users on 1/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/310:48 am
ORD
-
PHL
1 stop8h 00m
Spirit Airlines
mié. 2/412:40 pm
PHL
-
ORD
1 stop12h 07m
Spirit Airlines
Deal found 1/12$119
This Frontier deal was found by Cheapflights users on 1/11. 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.
mié. 2/116:15 am
MDW
-
PHL
1 stop9h 57m
Frontier
mar. 2/2411:40 am
PHL
-
MDW
1 stop8h 27m
Frontier
Deal found 1/11$128
This CheapOair deal was found by Cheapflights users on 1/12. 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.
mar. 2/31:20 pm
MDW
-
PHL
1 stop10h 22m
Frontier
mié. 2/46:00 am
PHL
-
MDW
1 stop7h 05m
Frontier
Deal found 1/12$129

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 enero 14, 2026.
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

lun. 2/9

6:20 am-6:11 pm

1 stop10h 51m

Philadelphia

mar. 2/24

11:40 am-7:07 pm

1 stop8h 27m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

mié. 2/4

6:20 pm-9:36 pm

Nonstop2h 16m

Philadelphia

jue. 2/5

1:10 pm-2:40 pm

Nonstop2h 30m

$217

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

vie. 3/13

6:08 pm-9:09 pm

Nonstop2h 01m

Philadelphia

dom. 3/15

6:30 am-8:00 am

Nonstop2h 30m

$217

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

mar. 4/7

1:55 pm-10:00 pm

1 stop7h 05m

Philadelphia

sáb. 4/11

7:45 am-8:50 am

Nonstop2h 05m

$227

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

jue. 2/5

1:45 pm-9:55 pm

1 stop7h 10m

Philadelphia

dom. 2/8

6:10 am-12:15 pm

1 stop7h 05m

$237

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 5/30

9:30 am-7:30 pm

1 stop9h 00m

Philadelphia

lun. 6/1

3:15 pm-7:26 pm

1 stop5h 11m

$246

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

vie. 1/30

10:00 am-12:55 pm

Nonstop1h 55m

Philadelphia

sáb. 2/7

12:40 pm-1:50 pm

Nonstop2h 10m

$247

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

vie. 1/30

6:20 pm-9:36 pm

Nonstop2h 16m

Philadelphia

sáb. 2/7

6:30 am-7:59 am

Nonstop2h 29m

$247

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

vie. 1/30

6:20 pm-9:36 pm

Nonstop2h 16m

Philadelphia

lun. 2/2

1:10 pm-2:40 pm

Nonstop2h 30m

$247

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

jue. 1/29

2:30 pm-5:34 pm

Nonstop2h 04m

Philadelphia

lun. 2/2

5:00 pm-6:30 pm

Nonstop2h 30m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 38 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 January 9, 2026.

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 $58). Flying from Chicago to Rehoboth Beach in June is currently the most expensive (average of $99). 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 enero 14, 2026.

It’s typically best to fly out from Chicago to Rehoboth Beach in the morning. Doing so could potentially save you 10% 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 January 10, 2026.

Travelers seeking maximum savings on their Chicago to Rehoboth Beach flight should consider departing on Monday 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 enero 14, 2026.

The most flights from CHI to R3H are scheduled on a Monday (41 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 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 enero 14, 2026.
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
4,257 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,156 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,118 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,309 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 2h 16m. The time it takes to get you to your destination can typically vary by up to 8h 35m. Airlines will cover a distance of 676 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 Frontier, which is currently one of the cheapest options available, starting at $49. American Airlines flights start at $80 while deals on Spirit Airlines start at $81 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 Malaysia Airlines (85%), Air Canada (77%) and Royal Jordanian (75%).

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

    The cheapest flight price from Chicago to Rehoboth Beach is $68. On average you can expect to pay $611. The most popular route, (Chicago O'Hare Intl - Philadelphia), can usually be booked for $106.

  • 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 $58). Flying from Chicago to Rehoboth Beach in June is currently the most expensive (average of $99). 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 enero 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$201FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$163FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$477FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$140Average$307FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$148Average$350FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$287FlexibilityNo cancel feeOn-time63%

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