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Delaware

$85+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$163
(Southwest)

One-way from

$85
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$207
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. 29% potential increase in price ($97 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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.
sáb. 8/91:05 pmMDW - PHL
Nonstop2h 00mSouthwest
mié. 8/135:55 amPHL - MDW
2 stops7h 45mSouthwest
Deal found 6/10$163
This United Airlines deal was found by Cheapflights users on 6/10. 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.
mié. 7/307:35 amORD - PHL
Nonstop2h 12mUnited Airlines
mié. 8/612:38 pmPHL - ORD
Nonstop2h 24mUnited Airlines
Deal found 6/10$164
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
jue. 7/104:26 pmORD - PHL
Nonstop2h 23mFrontier
dom. 7/138:39 pmPHL - ORD
Nonstop2h 36mFrontier
Deal found 6/10$165
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/295:00 amORD - PHL
Nonstop2h 00mAmerican Airlines
dom. 11/29:20 pmPHL - ORD
Nonstop2h 34mAmerican Airlines
Deal found 6/11$167
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/252:05 pmMDW - PHL
Nonstop2h 10mFrontier
jue. 8/285:40 amPHL - MDW
1 stop5h 28mFrontier
Deal found 6/11$174
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/95:05 amORD - PHL
1 stop10h 11mMultiple Airlines
lun. 7/215:48 pmPHL - ORD
Nonstop2h 39mMultiple Airlines
Deal found 6/12$182
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
mié. 7/95:05 amORD - PHL
1 stop10h 11mSpirit Airlines
lun. 7/149:12 pmPHL - ORD
1 stop10h 52mSpirit Airlines
Deal found 6/10$188
This Delta deal was found by Cheapflights users on 6/9. 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.
mié. 9/33:30 pmORD - PHL
1 stop5h 50mDelta
mar. 9/167:00 amPHL - ORD
1 stop8h 13mDelta
Deal found 6/9$197
This Delta deal was found by Cheapflights users on 6/10. 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.
vie. 10/36:00 amMDW - PHL
1 stop6h 28mDelta
mar. 10/72:40 pmPHL - MDW
1 stop8h 04mDelta
Deal found 6/10$207
This Southwest deal was found by Cheapflights users on 6/10. 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.
sáb. 8/24:20 pmORD - PHL
1 stop5h 05mSouthwest
lun. 8/45:30 amPHL - ORD
2 stops10h 30mSouthwest
Deal found 6/10$292
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/2612:37 pmORD - SBY
1 stop6h 53mAmerican Airlines
sáb. 8/27:18 pmSBY - ORD
1 stop4h 33mAmerican Airlines
Deal found 6/11$430

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 junio 12, 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

sáb. 8/9

1:05 pm-4:05 pm

Nonstop2h 00m

Philadelphia

mié. 8/13

5:55 am-12:40 pm

2 stops7h 45m

$163

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

mié. 7/30

7:35 am-10:47 am

Nonstop2h 12m

Philadelphia

mié. 8/6

12:38 pm-2:02 pm

Nonstop2h 24m

$164

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

jue. 7/10

4:26 pm-7:49 pm

Nonstop2h 23m

Philadelphia

dom. 7/13

8:39 pm-10:15 pm

Nonstop2h 36m

$165

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

dom. 8/10

6:55 am-10:03 am

Nonstop2h 08m

Philadelphia

sáb. 8/16

6:00 am-7:25 am

Nonstop2h 25m

$168

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

lun. 8/25

2:05 pm-5:15 pm

Nonstop2h 10m

Philadelphia

jue. 8/28

5:40 am-10:08 am

1 stop5h 28m

$174

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

mié. 7/9

5:05 am-4:16 pm

1 stop10h 11m

Philadelphia

lun. 7/21

5:48 pm-7:27 pm

Nonstop2h 39m

$182

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

mié. 7/9

5:05 am-4:16 pm

1 stop10h 11m

Philadelphia

lun. 7/14

9:12 pm-7:04 am

1 stop10h 52m

$188

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

mié. 9/3

3:30 pm-10:20 pm

1 stop5h 50m

Philadelphia

mar. 9/16

7:00 am-2:13 pm

1 stop8h 13m

$197

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

sáb. 7/12

5:53 pm-11:08 pm

1 stop4h 15m

Philadelphia

mar. 7/15

5:30 am-9:45 am

1 stop5h 15m

$209

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

mar. 9/2

6:00 am-2:30 pm

1 stop7h 30m

Philadelphia

mar. 9/16

8:15 am-9:30 pm

2 stops14h 15m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 25 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

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 junio 12, 2025.
To help decide which airline to fly from Chicago to Delaware, see what other customers have to say about Southwest, Delta and United Airlines. 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
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Frontier ($85), Spirit Airlines ($87), and United Airlines ($89).

  • 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$181Average$181FlexibilityNo cancel feeOn-time71%

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