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Delaware

$92+ Cheap flights from Chicago (CHI) to Delaware

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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Chicago to Delaware

Keep the following information in mind while searching for Chicago to Delaware flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Flightnetwork)

One-way from

$92
(Mytrip)

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 Delaware
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One-way flight from Chicago (CHI) to Delaware
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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 Delaware

Cheapest flights from Chicago to Delaware
Explore the most affordable flight options available from Chicago to Delaware. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/18. 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.
Fri 3/147:42 pmORD - PHL
1 stop12h 16mSpirit Airlines
Sat 3/226:34 pmPHL - ORD
1 stop15h 10mSpirit Airlines
Deal found 2/18$206
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/35:15 amMDW - PHL
1 stop19h 00mFrontier
Sun 4/611:57 amPHL - MDW
Nonstop2h 24mFrontier
Deal found 2/20$208
This Southwest deal was found by Cheapflights users on 2/19. 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 2/19$220
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/126:45 amORD - PHL
Nonstop2h 03mAmerican Airlines
Tue 4/157:25 amPHL - ORD
Nonstop2h 24mAmerican Airlines
Deal found 2/20$220
This United Airlines deal was found by Cheapflights users on 2/19. 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 4/111:10 amORD - PHL
Nonstop2h 08mUnited Airlines
Tue 4/810:43 amPHL - ORD
1 stop4h 27mUnited Airlines
Deal found 2/19$232
This Mytrip deal was found by Cheapflights users on 2/19. 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 3/310:02 amPHL - ORD
2 stops27h 35mMultiple Airlines
Deal found 2/19$235
This Delta deal was found by Cheapflights users on 2/19. 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 4/54:00 pmMDW - PHL
1 stop7h 48mDelta
Wed 4/96:00 amPHL - MDW
1 stop3h 43mDelta
Deal found 2/19$240
This eDestinos deal was found by Cheapflights users on 2/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/255:25 pmORD - PHL
2 stops36h 22mFrontier
Mon 4/288:31 pmPHL - ORD
1 stop15h 14mFrontier
Deal found 2/19$241
This Southwest deal was found by Cheapflights users on 2/19. 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 3/251:50 pmORD - PHL
1 stop7h 20mSouthwest
Wed 3/268:10 amPHL - ORD
2 stops14h 20mSouthwest
Deal found 2/19$314
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/71:00 pmORD - PHL
1 stop8h 02mJetBlue
Tue 3/1110:11 amPHL - ORD
1 stop7h 14mJetBlue
Deal found 2/19$334
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:51 amORD - SBY
1 stop7h 03mAmerican Airlines
Tue 9/161:50 pmSBY - ORD
1 stop4h 21mAmerican Airlines
Deal found 2/20$450

Find flights from Chicago to Delaware within your budget

Customize your flight search to find flights from Chicago to Delaware 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 20, 2025.

Fly from

Chicago

Fly to

Delaware

Route

Depart

Return

Price

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 3/14

7:42 pm-8:58 am

1 stop12h 16m

Philadelphia

Sat 3/22

6:34 pm-8:44 am

1 stop15h 10m

$206

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 4/3

5:15 am-1:15 am

1 stop19h 00m

Philadelphia

Sun 4/6

11:57 am-1:21 pm

Nonstop2h 24m

$208

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

Sat 4/12

6:45 am-9:48 am

Nonstop2h 03m

Philadelphia

Tue 4/15

7:25 am-8:49 am

Nonstop2h 24m

$220

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Tue 4/1

11:10 am-2:18 pm

Nonstop2h 08m

Philadelphia

Tue 4/8

10:43 am-2:10 pm

1 stop4h 27m

$232

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 6/13

10:57 am-2:15 pm

Nonstop2h 18m

Philadelphia

Mon 6/16

7:14 pm-12:08 am

1 stop5h 54m

$238

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 4/5

4:00 pm-12:48 am

1 stop7h 48m

Philadelphia

Wed 4/9

6:00 am-8:43 am

1 stop3h 43m

$240

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 3/8

7:42 pm-7:58 am

1 stop11h 16m

Philadelphia

Sat 3/15

5:40 am-12:10 pm

1 stop7h 30m

$260

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

Thu 3/6

1:00 pm-10:02 pm

1 stop8h 02m

Philadelphia

Tue 3/18

10:11 am-4:30 pm

1 stop7h 19m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 28 results
1
2
3

Best time to book a flight from Chicago to Delaware

Have a flexible travel schedule? Discover the best time to fly to Delaware 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 Delaware

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

Rainfall in Delaware by month

Plan your trip to Delaware by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Delaware ranges from 2.9 - 4.3 inches per month. July is typically the wettest month, when rainfall can reach 4.3 in. February is typically the driest time to visit Delaware when rainfall is around 2.9 in.

Temperature in Delaware by month

Plan your trip to Delaware by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Delaware, 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 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 32.0 F).

Reviews of airlines servicing Delaware

Get insights into the airlines that provide service to Delaware. 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 Delaware. Reviews last updated February 20, 2025.
To help decide which airline to fly from Chicago to Delaware, see what other customers have to say about Southwest, Alaska Airlines and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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 Delaware. 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 Delaware one-way?

    The cheapest airlines for a one-way flight from Chicago to Delaware are Spirit Airlines ($92), Frontier ($93), and Delta ($99).

  • What are the most popular routes from Chicago to Delaware?

    Most travelers choose Chicago O'Hare Intl - Philadelphia, Chicago Midway - Philadelphia or Chicago O'Hare Intl - Salisbury-Ocean City when deciding on the best route from Chicago to Delaware.

  • Can I find deals for flights from Chicago to Delaware that include hotel bookings?

    Yes. In addition to deals on Chicago to Delaware flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Delaware?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Delaware.

  • Can I find deals for business class flights from Chicago to Delaware?

    Yes. Cheapflights offers flight deals from Chicago to Delaware by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Chicago to Delaware

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Delaware

Discover the top airline that operate flights from Chicago to Delaware. 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$181Average$181FlexibilityNo cancel feeOn-time71%
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