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Delaware

$70+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
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 January 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 Delaware
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One-way flight from Chicago (CHI) to Delaware
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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 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 January 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.
Wed 2/412:44 pm
ORD
-
PHL
1 stop6h 04m
Multiple Airlines
Fri 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.
Fri 2/64:44 pm
ORD
-
PHL
Nonstop2h 15m
Multiple Airlines
Tue 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.
Fri 2/64:44 pm
ORD
-
PHL
Nonstop2h 15m
Multiple Airlines
Wed 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.
Wed 2/1110:48 am
ORD
-
PHL
1 stop8h 00m
Spirit Airlines
Wed 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.
Wed 2/48:10 am
ORD
-
PHL
1 stop6h 27m
Frontier
Fri 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.
Thu 3/123:21 pm
ORD
-
PHL
Nonstop2h 09m
Frontier
Sun 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.
Tue 1/2710:48 am
ORD
-
PHL
1 stop10h 15m
Multiple Airlines
Fri 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.
Fri 1/304:44 pm
ORD
-
PHL
Nonstop2h 15m
Frontier
Mon 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.
Fri 2/64:44 pm
ORD
-
PHL
Nonstop2h 15m
Frontier
Mon 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.
Tue 2/310:48 am
ORD
-
PHL
1 stop8h 00m
Spirit Airlines
Wed 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.
Wed 2/116:15 am
MDW
-
PHL
1 stop9h 57m
Frontier
Tue 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.
Tue 2/31:20 pm
MDW
-
PHL
1 stop10h 22m
Frontier
Wed 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 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 January 14, 2026.
Use the filters below to find and compare flights from Chicago to Delaware that are best for you.

Fly from

Chicago

Fly to

Delaware

Route

Depart

Return

Price

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 2/9

6:20 am-6:11 pm

1 stop10h 51m

Philadelphia

Tue 2/24

11:40 am-7:07 pm

1 stop8h 27m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 2/4

6:20 pm-9:36 pm

Nonstop2h 16m

Philadelphia

Thu 2/5

1:10 pm-2:40 pm

Nonstop2h 30m

$217

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 3/13

6:08 pm-9:09 pm

Nonstop2h 01m

Philadelphia

Sun 3/15

6:30 am-8:00 am

Nonstop2h 30m

$217

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 4/7

1:55 pm-10:00 pm

1 stop7h 05m

Philadelphia

Sat 4/11

7:45 am-8:50 am

Nonstop2h 05m

$227

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 2/5

1:45 pm-9:55 pm

1 stop7h 10m

Philadelphia

Sun 2/8

6:10 am-12:15 pm

1 stop7h 05m

$237

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 5/30

9:30 am-7:30 pm

1 stop9h 00m

Philadelphia

Mon 6/1

3:15 pm-7:26 pm

1 stop5h 11m

$246

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 1/30

10:00 am-12:55 pm

Nonstop1h 55m

Philadelphia

Sat 2/7

12:40 pm-1:50 pm

Nonstop2h 10m

$247

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 1/30

6:20 pm-9:36 pm

Nonstop2h 16m

Philadelphia

Sat 2/7

6:30 am-7:59 am

Nonstop2h 29m

$247

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 1/30

6:20 pm-9:36 pm

Nonstop2h 16m

Philadelphia

Mon 2/2

1:10 pm-2:40 pm

Nonstop2h 30m

$247

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 1/29

2:30 pm-5:34 pm

Nonstop2h 04m

Philadelphia

Mon 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 46 results
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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?

    Frontier, United Airlines, and Southwest can get you from Chicago to Delaware in just under 2h 16m. Your travel time can differ by up to 8h 35m. There are 676 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 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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