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Rehoboth Beach

$90+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
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The best prices from Chicago to Rehoboth Beach are usually found in August or September, booked 83 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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Mytrip)

One-way from

$90
(American Airlines)

Popular in

February

Cheapest in

August

Average price

$361
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. 35% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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.
Mon 3/35:15 amORD - PHL
2 stops33h 48mSpirit Airlines
Thu 3/65:30 amPHL - ORD
1 stop9h 17mSpirit Airlines
Deal found 2/20$209
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 4/242:40 pmMDW - PHL
1 stop8h 50mFrontier
Mon 4/284:10 pmPHL - MDW
Nonstop2h 16mFrontier
Deal found 2/20$211
This Southwest deal was found by Cheapflights users on 2/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/17:00 pmMDW - PHL
Nonstop1h 50mSouthwest
Sat 4/56:55 amPHL - MDW
Nonstop2h 10mSouthwest
Deal found 2/21$220
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/16:26 pmORD - PHL
Nonstop2h 13mUnited Airlines
Sat 4/59:31 amPHL - ORD
Nonstop2h 24mUnited Airlines
Deal found 2/21$220
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Thu 3/279:45 amORD - PHL
Nonstop1h 58mAmerican Airlines
Tue 4/17:20 amPHL - ORD
Nonstop2h 28mAmerican Airlines
Deal found 2/22$222
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2310:20 amMDW - PHL
1 stop6h 40mDelta
Sun 4/276:00 amPHL - MDW
1 stop3h 40mDelta
Deal found 2/22$227
This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:45 pmORD - PHL
1 stop25h 19mMultiple Airlines
Mon 3/38:59 pmPHL - ORD
3 stops25h 34mMultiple Airlines
Deal found 2/21$240
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/245:30 pmORD - PHL
1 stop6h 19mDelta
Tue 4/15:30 amPHL - ORD
1 stop5h 36mDelta
Deal found 2/21$242
This Southwest deal was found by Cheapflights users on 2/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/271:50 pmORD - PHL
1 stop9h 20mSouthwest
Tue 4/12:10 pmPHL - ORD
2 stops8h 50mSouthwest
Deal found 2/21$273
This Frontier deal was found by Cheapflights users on 2/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2310:57 amORD - PHL
Nonstop2h 18mFrontier
Wed 7/303:20 pmPHL - ORD
Nonstop2h 33mFrontier
Deal found 2/22$276
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/128:10 pmORD - PHL
1 stop14h 00mSun Country Air
Mon 6/1612:05 pmPHL - ORD
1 stop8h 06mSun Country Air
Deal found 2/22$284

Find flights from Chicago to Rehoboth Beach within your budget

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 February 22, 2025.

Fly from

Chicago

Fly to

Rehoboth Beach

Route

Depart

Return

Price

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Mon 3/3

5:15 am-4:03 pm

2 stops33h 48m

Philadelphia

Thu 3/6

5:30 am-1:47 pm

1 stop9h 17m

$209

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 4/24

2:40 pm-12:30 am

1 stop8h 50m

Philadelphia

Mon 4/28

4:10 pm-5:26 pm

Nonstop2h 16m

$211

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 4/1

7:00 pm-9:50 pm

Nonstop1h 50m

Philadelphia

Sat 4/5

6:55 am-8:05 am

Nonstop2h 10m

$220

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Tue 4/1

6:26 pm-9:39 pm

Nonstop2h 13m

Philadelphia

Sat 4/5

9:31 am-10:55 am

Nonstop2h 24m

$220

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 3/27

9:45 am-12:43 pm

Nonstop1h 58m

Philadelphia

Tue 4/1

7:20 am-8:48 am

Nonstop2h 28m

$222

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 4/23

10:20 am-6:00 pm

1 stop6h 40m

Philadelphia

Sun 4/27

6:00 am-8:40 am

1 stop3h 40m

$227

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 2/28

6:45 pm-9:04 pm

1 stop25h 19m

Philadelphia

Mon 3/3

8:59 pm-9:33 pm

3 stops25h 34m

$240

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Mon 3/24

5:30 pm-12:49 am

1 stop6h 19m

Philadelphia

Tue 4/1

5:30 am-10:06 am

1 stop5h 36m

$242

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 3/27

1:50 pm-12:10 am

1 stop9h 20m

Philadelphia

Tue 4/1

2:10 pm-10:00 pm

2 stops8h 50m

$273

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sun 3/16

4:30 pm-3:16 pm

1 stop21h 46m

Philadelphia

Sat 3/22

5:30 am-1:08 pm

1 stop8h 38m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 23 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.

Travel insights for flights from Chicago to Rehoboth Beach

Get recent, data-driven insights about flights from Chicago to Rehoboth Beach including ideal travel times, pricing trends, and more.

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Rehoboth Beach, you should look to book at least 83 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 February 22, 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 February 22, 2025.

The most flights from CHI to R3H are scheduled on a Wednesday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 February 22, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Chicago to Rehoboth Beach. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 American Airlines, which is currently one of the cheapest options available, starting at $90. JetBlue flights start at $91 while deals on Spirit Airlines start at $92 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 Copa Airlines (100%), Spirit Airlines (100%) and Malaysia Airlines (87%).

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

    The cheapest flight price from Chicago to Rehoboth Beach is $98. On average you can expect to pay $614. The most popular route, (Chicago O'Hare Intl - Philadelphia), can usually be booked for $102.

  • 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$51Average$131FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$119Average$333FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$128Average$218FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$136Average$297FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$138Average$278FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$266FlexibilityNo cancel feeOn-timeN/A
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