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Delaware

$61+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
dic. 3 — dic. 101
mié. 12/3
mié. 12/10
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 noviembre 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(CheapOair)

One-way from

$61
(Priceline)

Popular in

March

Cheapest in

October

Average price

$227
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 ($57 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 November 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 noviembre 3, 2025.

This CheapOair deal was found by Cheapflights users on 11/1. 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.
sáb. 11/151:37 pmMDW - PHL
1 stop9h 36mFrontier
mié. 11/196:50 pmPHL - MDW
1 stop22h 40mFrontier
Deal found 11/1$110
This Priceline deal was found by Cheapflights users on 11/2. 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.
lun. 11/175:05 amORD - PHL
1 stop5h 24mFrontier
jue. 11/2012:00 pmPHL - ORD
1 stop6h 39mFrontier
Deal found 11/2$110
This Frontier deal was found by Cheapflights users on 11/2. 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. 12/46:15 amMDW - PHL
1 stop8h 44mFrontier
jue. 12/1111:07 amPHL - MDW
1 stop11h 46mFrontier
Deal found 11/2$111
This Priceline deal was found by Cheapflights users on 11/2. 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.
sáb. 12/63:26 pmORD - PHL
1 stop6h 50mMultiple Airlines
mar. 12/912:20 pmPHL - ORD
1 stop7h 26mMultiple Airlines
Deal found 11/2$112
This Kiwi.com deal was found by Cheapflights users on 11/2. 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. 12/122:00 pmORD - PHL
Nonstop2h 15mFrontier
dom. 12/146:00 amPHL - ORD
1 stop6h 28mFrontier
Deal found 11/2$115
This Kiwi.com deal was found by Cheapflights users on 11/2. 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. 11/218:41 pmMDW - PHL
Nonstop1h 57mFrontier
lun. 11/244:50 pmPHL - MDW
Nonstop2h 16mFrontier
Deal found 11/2$117
This CheapOair deal was found by Cheapflights users on 10/31. 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.
jue. 12/411:44 amORD - PHL
1 stop12h 07mFrontier
vie. 12/511:10 amPHL - ORD
Nonstop2h 30mFrontier
Deal found 10/31$117
This Kiwi.com deal was found by Cheapflights users on 11/1. 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. 11/148:26 amORD - PHL
Nonstop2h 13mFrontier
jue. 11/206:47 pmPHL - ORD
1 stop6h 21mFrontier
Deal found 11/1$118
This CheapOair deal was found by Cheapflights users on 11/2. 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.
dom. 11/168:32 amMDW - PHL
Nonstop2h 02mFrontier
mié. 11/196:50 pmPHL - MDW
1 stop22h 40mFrontier
Deal found 11/2$119
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
lun. 12/153:23 pmORD - PHL
Nonstop2h 15mMultiple Airlines
mié. 12/173:45 pmPHL - ORD
1 stop9h 24mMultiple Airlines
Deal found 11/2$119
This Frontier deal was found by Cheapflights users on 11/2. 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. 12/122:00 pmORD - PHL
Nonstop2h 15mFrontier
mar. 12/1612:20 pmPHL - ORD
1 stop7h 26mFrontier
Deal found 11/2$120
This Priceline deal was found by Cheapflights users on 11/2. 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.
lun. 12/15:30 amORD - PHL
Nonstop2h 07mFrontier
lun. 12/812:33 pmPHL - ORD
Nonstop2h 30mFrontier
Deal found 11/2$123

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 noviembre 3, 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

mar. 12/2

11:05 am-2:00 pm

Nonstop1h 55m

Philadelphia

mar. 12/9

6:15 pm-7:25 pm

Nonstop2h 10m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 1/24

11:20 am-2:31 pm

Nonstop2h 11m

Philadelphia

sáb. 1/31

10:10 am-11:38 am

Nonstop2h 28m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

mié. 12/17

8:10 am-11:05 am

Nonstop1h 55m

Philadelphia

mié. 12/17

4:00 pm-5:10 pm

Nonstop2h 10m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 1/17

2:30 pm-5:34 pm

Nonstop2h 04m

Philadelphia

dom. 1/18

10:10 am-11:38 am

Nonstop2h 28m

$139

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

jue. 11/13

9:15 am-12:19 pm

Nonstop2h 04m

Philadelphia

lun. 11/17

7:00 am-5:01 pm

1 stop11h 01m

$154

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

vie. 12/5

9:00 am-12:07 pm

Nonstop2h 07m

Philadelphia

sáb. 12/6

5:07 pm-6:36 pm

Nonstop2h 29m

$158

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

jue. 11/13

9:15 am-12:19 pm

Nonstop2h 04m

Philadelphia

sáb. 11/15

6:19 am-11:30 am

1 stop30h 11m

$172

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

mié. 12/17

6:00 am-1:19 pm

1 stop6h 19m

Philadelphia

mié. 12/17

6:07 pm-11:47 pm

1 stop6h 40m

$177

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

sáb. 1/17

5:55 pm-12:23 am

1 stop5h 28m

Philadelphia

dom. 1/18

12:11 pm-7:35 pm

1 stop8h 24m

$177

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

jue. 11/27

9:42 am-5:36 pm

1 stop6h 54m

Philadelphia

mar. 12/2

6:55 am-12:10 pm

1 stop6h 15m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 43 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 noviembre 3, 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
11,038 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

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
11,038 reviews
American Airlines
7.2
Good
11,038 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

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?

    Southwest, United Airlines, and Frontier 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 cheapest airlines to fly from Chicago to Delaware one-way?

    The cheapest airlines for a one-way flight from Chicago to Delaware are Frontier ($63), Southwest ($70), and United Airlines ($70).

  • 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 noviembre 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$181Average$181FlexibilityNo cancel feeOn-time71%

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