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Delaware

$77+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
May 24 — May 311
Sun 5/24
Sun 5/31
1 adult, Economy
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Cheap 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 April 24, 2026.

This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:52 pm
ORD
-
PHL
Nonstop2h 28m
Frontier
Sat 6/275:34 pm
PHL
-
ORD
1 stop6h 45m
Frontier
Deal found 4/20$184
This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:50 pm
ORD
-
PHL
1 stop7h 20m
Frontier
Fri 5/298:30 am
PHL
-
ORD
1 stop12h 11m
Frontier
Deal found 4/20$185
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sat 5/302:15 pm
MDW
-
PHL
1 stop6h 20m
Southwest
Wed 6/311:35 am
PHL
-
MDW
Nonstop2h 05m
Southwest
Deal found 4/23$187
This Frontier deal was found by Cheapflights users on 4/22. 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.
Thu 4/231:12 pm
ORD
-
PHL
1 stop8h 43m
Frontier
Mon 4/276:29 pm
PHL
-
ORD
Nonstop2h 34m
Frontier
Deal found 4/22$187
This Trip.com deal was found by Cheapflights users on 4/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
-
PHL
1 stop6h 15m
Frontier
Thu 5/74:35 pm
PHL
-
MDW
1 stop6h 27m
Frontier
Deal found 4/19$188
This Super.com deal was found by Cheapflights users on 4/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:28 pm
ORD
-
PHL
1 stop7h 26m
Frontier
Sun 5/36:29 pm
PHL
-
ORD
Nonstop2h 34m
Frontier
Deal found 4/20$188
This Southwest deal was found by Cheapflights users on 4/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/192:50 pm
MDW
-
PHL
Nonstop2h 00m
Southwest
Tue 5/266:45 pm
PHL
-
MDW
1 stop4h 30m
Southwest
Deal found 4/20$189
This Frontier deal was found by Cheapflights users on 4/22. 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.
Fri 6/127:52 pm
ORD
-
PHL
Nonstop2h 28m
Frontier
Mon 6/151:32 pm
PHL
-
ORD
1 stop7h 21m
Frontier
Deal found 4/22$189
This Super.com deal was found by Cheapflights users on 4/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:56 pm
ORD
-
PHL
Nonstop2h 26m
Frontier
Thu 5/145:13 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Deal found 4/22$190
This CheapOair deal was found by Cheapflights users on 4/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:41 am
MDW
-
PHL
1 stop23h 18m
Frontier
Sat 5/94:35 pm
PHL
-
MDW
1 stop6h 27m
Frontier
Deal found 4/20$191
This Super.com deal was found by Cheapflights users on 4/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:52 pm
ORD
-
PHL
Nonstop2h 26m
Frontier
Thu 5/147:45 am
PHL
-
ORD
1 stop7h 54m
Frontier
Deal found 4/21$191
This CheapOair deal was found by Cheapflights users on 4/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:19 pm
MDW
-
PHL
1 stop5h 55m
Frontier
Sun 5/1712:59 pm
PHL
-
MDW
1 stop27h 58m
Frontier
Deal found 4/20$192

Find flight deals from Chicago to Delaware

Keep the following information in mind while searching for Chicago to Delaware flight deals. Data was last updated April 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$184
(Frontier)

One-way from

$77
(Expedia)

Popular in

March

Cheapest in

October

Average price

$299
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
Search Deals
From Chicago (CHI) to Delaware
Search Deals
One-way flight from Chicago (CHI) to Delaware
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
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 April 24, 2026.
Use the filters below to find and compare flights from Chicago to Delaware that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Tue 9/15

9:06 am-12:23 pm

Nonstop2h 17m

Philadelphia

Wed 9/16

9:52 am-11:15 am

Nonstop2h 23m

$239

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 5/12

4:40 pm-10:00 pm

1 stop4h 20m

Philadelphia

Wed 5/13

2:00 pm-3:10 pm

Nonstop2h 10m

$247

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 5/15

7:00 am-10:14 am

Nonstop2h 14m

Philadelphia

Tue 5/19

11:32 am-1:01 pm

Nonstop2h 29m

$257

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 7/11

6:35 pm-11:16 pm

1 stop3h 41m

Philadelphia

Wed 7/15

9:46 am-12:33 pm

1 stop3h 47m

$267

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 5/23

5:19 pm-11:07 pm

1 stop4h 48m

Philadelphia

Mon 5/25

5:17 am-10:16 am

1 stop5h 59m

$269

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 6/12

1:50 pm-10:29 pm

1 stop7h 39m

Philadelphia

Wed 6/17

7:20 am-7:53 pm

2 stops13h 33m

$272

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 5/23

6:08 pm-9:28 pm

Nonstop2h 20m

Philadelphia

Mon 5/25

6:00 am-7:29 am

Nonstop2h 29m

$273

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 8/14

3:56 pm-7:19 pm

Nonstop2h 23m

Philadelphia

Sat 8/15

6:44 pm-8:12 pm

Nonstop2h 28m

$291

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 6/12

9:33 pm-12:45 am

Nonstop2h 12m

Philadelphia

Wed 6/17

6:00 am-7:29 am

Nonstop2h 29m

$291

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 5/22

5:19 pm-11:07 pm

1 stop4h 48m

Philadelphia

Sun 5/24

6:12 am-10:29 am

1 stop5h 17m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 58 resultsSorted by cheapest first
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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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Delaware
No data available for this route at this time. Please check back soon.

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.

  • How long is the flight from Chicago to Delaware?

    United Airlines, Southwest, and Delta can get you from Chicago to Delaware in just under 1h 55m. Your travel time can differ by up to 2h 53m. There are 666 mi between Chicago and Delaware. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Turkish Airlines ($406), Qatar Airways ($418), and Royal Jordanian ($427).

  • 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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