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Delaware

$84+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$166
(FlightHub)

One-way from

$84
(Cheapflightsfares)

Popular in

March

Cheapest in

August

Average price

$214
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. 31% potential increase in price ($102 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 May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Wed 8/138:00 amORD - PHL
1 stop7h 33mMultiple Airlines
Mon 8/185:48 pmPHL - ORD
Nonstop2h 39mMultiple Airlines
Deal found 4/30$166
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Fri 5/168:26 pmORD - PHL
Nonstop2h 08mFrontier
Mon 5/195:01 pmPHL - ORD
Nonstop2h 28mFrontier
Deal found 4/30$172
This Frontier deal was found by Cheapflights users on 4/30. 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 5/242:44 pmMDW - PHL
1 stop13h 23mFrontier
Mon 5/266:39 pmPHL - MDW
Nonstop2h 16mFrontier
Deal found 4/30$178
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 5/218:25 amMDW - PHL
Nonstop2h 00mSouthwest
Sun 5/256:55 pmPHL - MDW
Nonstop2h 15mSouthwest
Deal found 4/30$180
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/217:00 amORD - PHL
Nonstop2h 04mAmerican Airlines
Sun 5/257:20 amPHL - ORD
Nonstop2h 26mAmerican Airlines
Deal found 4/30$180
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/287:47 amORD - PHL
1 stop23h 01mSpirit Airlines
Tue 6/35:45 amPHL - ORD
1 stop28h 05mSpirit Airlines
Deal found 4/30$181
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 6/3011:20 amORD - PHL
Nonstop2h 09mUnited Airlines
Tue 7/15:11 pmPHL - ORD
Nonstop2h 24mUnited Airlines
Deal found 4/30$189
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/216:00 amMDW - PHL
1 stop7h 29mDelta
Sun 5/259:59 amPHL - MDW
1 stop3h 29mDelta
Deal found 4/30$208
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/217:10 amORD - PHL
1 stop3h 50mDelta
Sun 5/251:15 pmPHL - ORD
1 stop6h 33mDelta
Deal found 4/30$208
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 6/304:00 pmORD - PHL
1 stop6h 30mSouthwest
Tue 7/15:30 amPHL - ORD
2 stops10h 30mSouthwest
Deal found 4/30$304
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:36 pmMDW - PHL
2 stops23h 58mMultiple Airlines
Mon 6/95:45 amPHL - MDW
2 stops15h 01mMultiple Airlines
Deal found 4/30$350
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 5/243:01 pmORD - SBY
1 stop4h 32mAmerican Airlines
Sat 5/314:36 pmSBY - ORD
1 stop6h 07mAmerican Airlines
Deal found 4/29$432

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 May 1, 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

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 5/29

10:00 am-5:27 pm

1 stop6h 27m

Philadelphia

Fri 5/30

3:39 pm-5:01 pm

Nonstop2h 22m

$169

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 5/16

8:26 pm-11:34 pm

Nonstop2h 08m

Philadelphia

Sun 5/18

7:15 am-8:43 am

Nonstop2h 28m

$172

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 5/24

2:44 pm-5:07 am

1 stop13h 23m

Philadelphia

Mon 5/26

6:39 pm-7:55 pm

Nonstop2h 16m

$178

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 5/21

8:25 am-11:25 am

Nonstop2h 00m

Philadelphia

Sun 5/25

6:55 pm-8:10 pm

Nonstop2h 15m

$180

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 5/21

7:00 am-10:04 am

Nonstop2h 04m

Philadelphia

Sun 5/25

7:20 am-8:46 am

Nonstop2h 26m

$180

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 5/28

7:47 am-7:48 am

1 stop23h 01m

Philadelphia

Tue 6/3

5:45 am-8:50 am

1 stop28h 05m

$181

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Mon 6/30

11:20 am-2:29 pm

Nonstop2h 09m

Philadelphia

Tue 7/1

5:11 pm-6:35 pm

Nonstop2h 24m

$189

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Wed 5/21

6:00 am-2:29 pm

1 stop7h 29m

Philadelphia

Sun 5/25

9:59 am-12:28 pm

1 stop3h 29m

$208

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 5/21

7:10 am-12:00 pm

1 stop3h 50m

Philadelphia

Sun 5/25

1:15 pm-6:48 pm

1 stop6h 33m

$208

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Mon 6/30

4:00 pm-11:30 pm

1 stop6h 30m

Philadelphia

Tue 7/1

5:30 am-3:00 pm

2 stops10h 30m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 25 results
1
2
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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 May 1, 2025.
To help decide which airline to fly from Chicago to Delaware, see what other customers have to say about Alaska Airlines, Southwest and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Spirit Airlines ($84), Frontier ($85), and Southwest ($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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$181Average$181FlexibilityNo cancel feeOn-time71%

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