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$38 Find Cheap Flights from Chicago to Wilmington

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Wilmington departing on 11/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Good to know

Low season

January

High season

November

Cheapest flight

$38
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 12% increase in price.
Flight from Chicago Midway Airport to Philadelphia

When to book flights from Chicago to Wilmington

Are your dates flexible? Find out the best times to travel from Chicago to Wilmington based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Wilmington

  • Which airports will I be using when flying from Chicago to Wilmington?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Wilmington does not have its own airport so you’ll be flying into nearby Philadelphia airport, which is 18.6 mi away.

  • How long does a flight from Chicago to Wilmington take?

    Direct flights cover the 661 miles separating Chicago and Wilmington in about 1h 55m.

  • How many flights are there between Chicago and Wilmington?

    62 direct flights run between Chicago and Wilmington on a daily basis. On average, there are about 436 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Wilmington?

    Consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Wilmington?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Wilmington.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Wilmington?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Wilmington from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Wilmington?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Wilmington with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Wilmington?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Wilmington from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Wilmington?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Wilmington found on KAYAK was with Frontier for $38. Frontier offered a round-trip connection from $72 and United Airlines from $132.

See more FAQs

Top tips for finding cheap flights from Chicago to Wilmington

  • There is no airport in Wilmington. Instead, you’ll be flying into Philadelphia Airport when flying between Chicago and Wilmington.
  • The cheapest flight from Chicago to Wilmington was found 69 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, February and March. The cheapest month to fly is August.
See more tips

Top 5 airlines serving Chicago to Wilmington

Need help choosing which airline to fly with from Chicago to Wilmington? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
SouthwestOverall score based on 5083 reviews
7.2Food
8.7Crew
8.1Comfort
8.3Boarding
7.7Entertainment
Airline reviews

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

10.0 ExcellentDouglas, Nov 2024PVD - MCO
Read more Southwest reviews

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a hell hole of an airport. It is the new LaGuardia. Everything Cobbled together. Security gates closed. Terri directional signage

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

The fluidity of the entire process of boarding the plane the flight attendants attentiveness. The flight attendants also provided coloring books for my kids who loved it.

I used to fly SWA all the time. I know the crew has their little acts that are often fun, and entertaining. On this flight one of the crew was just not nice. Very surprising.

It was really nice! I appreciate the gate attendant allowing families with small children to board early on in the process… that was very helpful! The internet service didn’t work with the app I was trying to use even though I paid the $8… other than that it was great! Oh and I should’ve asked for the whole cranberry cocktail can. That cup was about 2 sips…

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

Flight did not have seat back entertainment and the wifi was iffy.

Pretty standard flight. Delta has a good selection of movies.

The WiFi has been awful on my last few Delta Air Lines flights.

The seats are uncomfortable, feels like a small seat pad on plywood.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Didn't make it dir to delays - no support from United staff

My flight was delayed for a whole day, so I lost a day of my vacation.

flight delayed, was put on another flight after standby queue, luggage was misplaced and arrived to me 3 days later

The baggage handlers broke the handle on my bag that they put under the plane that I checked on the jetway. They traded it out for a less quality bag in Tulsa. But, they said they would try to fix it. Bologna! There was no fixing that bag handle. Someone didn’t care how they treated the bag.

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

BAD. As a family could not sit together. The gate agent told us there was only one seat in the middle left, when we got on the plane the situation was very different with whole rows of seats empty

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

Book cheap flights from Chicago to Wilmington

Recent round-trip flight deals

2/13Thu
nonstopFrontier
2h 03mORD-PHL
2/18Tue
nonstopFrontier
2h 24mPHL-ORD
$72
12/16Mon
nonstopFrontier
2h 07mORD-PHL
12/18Wed
nonstopFrontier
2h 28mPHL-ORD
$76
1/28Tue
nonstopUnited Airlines
2h 04mORD-PHL
1/28Tue
nonstopUnited Airlines
2h 31mPHL-ORD
$132
12/11Wed
nonstopUnited Airlines
2h 00mORD-PHL
12/14Sat
nonstopUnited Airlines
2h 24mPHL-ORD
$137
12/9Mon
nonstopAmerican Airlines
2h 00mORD-PHL
12/10Tue
nonstopAmerican Airlines
2h 30mPHL-ORD
$149
12/3Tue
nonstopAmerican Airlines
1h 56mORD-PHL
12/9Mon
nonstopAmerican Airlines
2h 30mPHL-ORD
$161
12/4Wed
nonstopSouthwest
1h 55mMDW-PHL
12/5Thu
nonstopSouthwest
2h 10mPHL-MDW
$162
12/6Fri
1 stopDelta
4h 29mMDW-PHL
12/13Fri
1 stopDelta
5h 20mPHL-MDW
$196
12/7Sat
1 stopDelta
4h 59mORD-PHL
12/8Sun
1 stopDelta
7h 36mPHL-ORD
$196
11/18Mon
nonstopSouthwest
1h 55mMDW-PHL
11/20Wed
nonstopSouthwest
2h 10mPHL-MDW
$215

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Recent one-way flight deals

11/23Sat
nonstopFrontier
2h 01mMDW-PHL
$38
11/14Thu
nonstopFrontier
1h 59mORD-PHL
$38
12/7Sat
nonstopUnited Airlines
2h 03mORD-PHL
$69
12/10Tue
nonstopSouthwest
1h 50mMDW-PHL
$69
1/9Thu
nonstopUnited Airlines
2h 10mORD-PHL
$81
1/9Thu
nonstopSouthwest
1h 50mMDW-PHL
$81
12/17Tue
1 stopDelta
5h 51mORD-PHL
$97
12/4Wed
1 stopDelta
5h 06mMDW-PHL
$98
11/26Tue
nonstopAmerican Airlines
1h 56mORD-PHL
$136
11/23Sat
nonstopAmerican Airlines
1h 56mORD-PHL
$153

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Last minute flights from Chicago to Wilmington

Last minute flight, train and bus deals

11/11Mon
nonstopFrontier
2h 06mORD-PHL
11/14Thu
nonstopFrontier
2h 26mPHL-ORD
$103
11/9Sat
nonstopFrontier
1h 58mMDW-PHL
11/16Sat
nonstopFrontier
2h 17mPHL-MDW
$109
11/12Tue
nonstopUnited Airlines
2h 04mORD-PHL
11/16Sat
nonstopUnited Airlines
2h 20mPHL-ORD
$227
11/12Tue
nonstopUnited Airlines
2h 04mORD-PHL
11/16Sat
multi-stopUnited Airlines
4h 09mPHL-ORD
$237
11/12Tue
multi-stopDelta
5h 01mORD-PHL
11/16Sat
multi-stopDelta
6h 20mPHL-ORD
$246
11/12Tue
nonstopSouthwest
1h 50mMDW-PHL
11/13Wed
nonstopSouthwest
2h 10mPHL-MDW
$390
11/12Tue
multi-stopSouthwest
10h 45mMDW-PHL
11/13Wed
nonstopSouthwest
2h 10mPHL-MDW
$404
11/12Tue
nonstopAmerican Airlines
1h 54mORD-PHL
11/19Tue
nonstopAmerican Airlines
2h 38mPHL-ORD
$406
11/12Tue
multi-stopAmerican Airlines
4h 05mORD-PHL
11/19Tue
nonstopAmerican Airlines
2h 38mPHL-ORD
$415
11/11Mon
multi-stopDelta
4h 35mMDW-PHL
11/13Wed
multi-stopDelta
5h 14mPHL-MDW
$606

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Everything you need to know for your flight from Chicago to Wilmington