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Delaware

$69+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$120
(Trip.com)

One-way from

$69
(Cheapflightsfares)

Popular in

March

Cheapest in

October

Average price

$185
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. 21% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 15, 2025.

This Trip.com deal was found by Cheapflights users on 9/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/236:24 pmMDW - PHL
1 stop9h 55mFrontier
dom. 10/266:10 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/12$120
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1711:50 amORD - PHL
Nonstop2h 09mFrontier
dom. 10/196:00 amPHL - ORD
1 stop6h 18mFrontier
Deal found 9/13$120
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1711:50 amORD - PHL
Nonstop2h 09mFrontier
vie. 10/175:12 pmPHL - ORD
1 stop9h 19mFrontier
Deal found 9/14$121
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/37:15 amMDW - PHL
1 stop8h 17mFrontier
lun. 10/66:00 amPHL - MDW
Nonstop2h 11mFrontier
Deal found 9/14$122
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
vie. 11/145:11 amORD - PHL
1 stop5h 18mFrontier
lun. 11/176:00 amPHL - ORD
Nonstop2h 26mFrontier
Deal found 9/14$122
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/38:15 amMDW - PHL
Nonstop2h 01mFrontier
dom. 10/56:00 amPHL - MDW
Nonstop2h 11mFrontier
Deal found 9/14$123
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1711:50 amORD - PHL
Nonstop2h 09mFrontier
mié. 10/2210:49 amPHL - ORD
1 stop6h 51mFrontier
Deal found 9/14$123
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
vie. 10/1012:13 pmMDW - PHL
Nonstop2h 00mFrontier
lun. 10/134:13 pmPHL - MDW
Nonstop2h 14mFrontier
Deal found 9/14$124
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1011:51 amORD - PHL
Nonstop2h 09mFrontier
dom. 10/2610:02 pmPHL - ORD
1 stop10h 08mFrontier
Deal found 9/13$124
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
vie. 10/175:28 pmMDW - PHL
1 stop6h 39mFrontier
dom. 10/196:10 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 9/14$125
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1711:50 amORD - PHL
Nonstop2h 09mFrontier
jue. 10/234:10 pmPHL - ORD
Nonstop2h 30mFrontier
Deal found 9/14$125
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/69:15 amMDW - PHL
Nonstop2h 04mFrontier
dom. 11/94:47 pmPHL - MDW
1 stop8h 43mFrontier
Deal found 9/13$126

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 septiembre 15, 2025.
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

lun. 9/29

8:15 am-11:16 am

Nonstop2h 01m

Philadelphia

mié. 10/8

9:14 pm-9:47 am

1 stop13h 33m

$147

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

sáb. 10/11

5:35 pm-8:30 pm

Nonstop1h 55m

Philadelphia

sáb. 10/25

5:10 pm-6:15 pm

Nonstop2h 05m

$149

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

jue. 11/6

11:45 am-2:40 pm

Nonstop1h 55m

Philadelphia

sáb. 11/8

5:35 pm-6:45 pm

Nonstop2h 10m

$158

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

vie. 10/17

9:15 pm-12:10 am

Nonstop1h 55m

Philadelphia

mar. 10/21

6:05 pm-7:10 pm

Nonstop2h 05m

$158

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

jue. 9/25

4:56 pm-12:57 am

1 stop7h 01m

Philadelphia

lun. 9/29

1:02 pm-11:20 pm

1 stop11h 18m

$162

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

lun. 10/13

9:15 pm-12:10 am

Nonstop1h 55m

Philadelphia

sáb. 10/18

6:00 am-7:05 am

Nonstop2h 05m

$178

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 9/27

7:30 am-10:39 am

Nonstop2h 09m

Philadelphia

dom. 10/5

6:30 am-7:53 am

Nonstop2h 23m

$179

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

mar. 10/14

5:45 am-11:20 am

1 stop4h 35m

Philadelphia

sáb. 10/18

12:05 pm-1:10 pm

Nonstop2h 05m

$179

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 1/24

1:45 pm-7:55 pm

1 stop5h 10m

Philadelphia

jue. 1/29

6:10 am-12:15 pm

1 stop7h 05m

$182

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 10/4

7:30 am-10:39 am

Nonstop2h 09m

Philadelphia

mié. 10/8

6:30 am-7:52 am

Nonstop2h 22m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 48 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.

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 septiembre 15, 2025.
Peruse reviews from past customers who have flown with American Airlines from Chicago to Delaware to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Overall

7.2

Comfort

7.2

Boarding

7.5

Crew

8.0

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Overall

7.2

Comfort

7.2

Boarding

7.5

Crew

8.0

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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, Southwest, and United Airlines can get you from Chicago to Delaware in just under 1h 55m. Your travel time will be generally consistent. There are 666 mi between Chicago and Delaware. Most flights are nonstop.

  • 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$181Average$181FlexibilityNo cancel feeOn-time71%

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