HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Delaware

$77+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ILG
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Delaware with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 31, 2025.

Round-trip from

$140
(Frontier)

One-way from

$77
(Frontier)

Popular in

March

Cheapest in

September

Average price

$202
From Chicago (CHI) to Delaware
Search Deals
One-way flight from Chicago (CHI) to Delaware
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 31, 2025.

This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/158:27 pmORD - PHL
Nonstop2h 26mFrontier
Sun 8/179:19 pmPHL - ORD
Nonstop2h 35mFrontier
Deal found 7/31$140
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Thu 10/168:15 amMDW - PHL
Nonstop2h 02mFrontier
Sun 10/196:05 amPHL - MDW
Nonstop2h 15mFrontier
Deal found 7/30$142
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:05 pmORD - PHL
1 stop10h 54mMultiple Airlines
Thu 10/1610:21 amPHL - ORD
Nonstop2h 31mMultiple Airlines
Deal found 7/29$154
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/168:12 pmORD - PHL
1 stop12h 44mSpirit Airlines
Mon 8/182:06 pmPHL - ORD
1 stop10h 53mSpirit Airlines
Deal found 7/29$165
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:30 amMDW - PHL
Nonstop1h 55mSouthwest
Sat 10/186:00 amPHL - MDW
Nonstop2h 05mSouthwest
Deal found 7/31$177
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/309:11 pmORD - PHL
Nonstop2h 13mAmerican Airlines
Mon 9/16:00 amPHL - ORD
Nonstop2h 25mAmerican Airlines
Deal found 7/29$177
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:25 pmMDW - PHL
1 stop4h 55mDelta
Sun 8/316:00 amPHL - MDW
1 stop6h 34mDelta
Deal found 7/31$197
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 10/711:50 amORD - SBY
1 stop4h 29mAmerican Airlines
Sun 10/128:00 amSBY - ORD
1 stop5h 04mAmerican Airlines
Deal found 7/29$450

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 July 31, 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

Fri 8/15

8:27 pm-11:53 pm

Nonstop2h 26m

Philadelphia

Sun 8/17

9:19 pm-10:54 pm

Nonstop2h 35m

$140

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Thu 10/16

8:15 am-11:17 am

Nonstop2h 02m

Philadelphia

Sun 10/19

6:05 am-7:20 am

Nonstop2h 15m

$142

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 10/2

12:05 pm-11:59 pm

1 stop10h 54m

Philadelphia

Thu 10/16

10:21 am-11:52 am

Nonstop2h 31m

$154

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 8/16

8:12 pm-9:56 am

1 stop12h 44m

Philadelphia

Mon 8/18

2:06 pm-11:59 pm

1 stop10h 53m

$165

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Fri 10/10

6:30 am-9:25 am

Nonstop1h 55m

Philadelphia

Sat 10/18

6:00 am-7:05 am

Nonstop2h 05m

$177

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 8/30

7:24 pm-10:38 pm

Nonstop2h 14m

Philadelphia

Tue 9/2

9:15 pm-10:49 pm

Nonstop2h 34m

$177

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Sat 8/30

4:25 pm-10:20 pm

1 stop4h 55m

Philadelphia

Sun 8/31

6:00 am-11:34 am

1 stop6h 34m

$197

ChicagoSalisbury

ORD - SBY

ORDSBY

Chicago O'Hare Intl

Tue 10/7

11:50 am-5:19 pm

1 stop4h 29m

Salisbury-Ocean City

Sun 10/12

8:00 am-12:04 pm

1 stop5h 04m

$450

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 8/25

2:05 pm-5:15 pm

Nonstop2h 10m

$77

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Thu 8/21

6:35 am-9:52 am

Nonstop2h 17m

$78

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 18 results
1
2

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 July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 ($77), Spirit Airlines ($80), 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Delaware

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Seattle flights
O'Hare Intl to Denver flights
O'Hare Intl to Boston flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Orlando flights
Midway to Las Vegas flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Midway to LaGuardia flights
Midway to Newark flights
O'Hare Intl to San Francisco flights
O'Hare Intl to San Diego flights
O'Hare Intl to Ontario flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Dulles Intl flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Atlanta flights
St. Louis to Las Vegas flights
O'Hare Intl to Santa Ana flights
Midway to Miami flights
O'Hare Intl to Nashville flights
O'Hare Intl to Portland flights
O'Hare Intl to Tampa flights
O'Hare Intl to Austin flights
Midway to Orlando flights
O'Hare Intl to Baltimore flights
St. Louis to Seattle flights
O'Hare Intl to Hobby flights
O'Hare Intl to George Bush Intcntl flights
Midway to Dallas/Fort Worth flights
Midway to Denver flights
Midway to Seattle flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Raleigh flights
Midway to Atlanta flights
Midway to San Francisco flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Love Field flights
O'Hare Intl to Burbank flights
St. Louis to LaGuardia flights

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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$181Average$181FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.