$28 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 12/24. 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

July

Cheapest flight

$28
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 14% lower on average.
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?

    66 direct flights run between Chicago and Wilmington on a daily basis. On average, there are about 462 departures each week.

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

    Consider leaving on a Tuesday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

  • 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 $28. Frontier offered a round-trip connection from $67 and American Airlines from $137.

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 5015 reviews
8.7Crew
8.1Comfort
8.2Boarding
7.7Entertainment
7.2Food
Airline reviews

This was a nicer flight - not fully booked and so we were able to spread out.

10.0 ExcellentJohn, Nov 2024LAS - IND
Read more Southwest reviews

This was a nicer flight - not fully booked and so we were able to spread out.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

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.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

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.

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.

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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.

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

12/17Tue
nonstopFrontier
2h 03mMDW-PHL
12/19Thu
nonstopFrontier
2h 24mPHL-MDW
$67
12/12Thu
nonstopFrontier
2h 06mMDW-PHL
12/17Tue
nonstopFrontier
2h 26mPHL-MDW
$68
1/8Wed
nonstopAmerican Airlines
2h 01mORD-PHL
1/11Sat
nonstopAmerican Airlines
2h 29mPHL-ORD
$137
12/14Sat
nonstopAmerican Airlines
2h 01mORD-PHL
1/11Sat
nonstopAmerican Airlines
2h 29mPHL-ORD
$154
1/17Fri
nonstopSouthwest
1h 55mMDW-PHL
1/21Tue
nonstopSouthwest
2h 15mPHL-MDW
$158
12/11Wed
nonstopSouthwest
1h 55mMDW-PHL
12/17Tue
nonstopSouthwest
2h 10mPHL-MDW
$172
12/12Thu
nonstopUnited Airlines
2h 00mORD-PHL
12/17Tue
1 stopUnited Airlines
4h 49mPHL-ORD
$181
12/11Wed
1 stopDelta
6h 02mMDW-PHL
12/17Tue
1 stopDelta
5h 24mPHL-MDW
$196
12/3Tue
1 stopDelta
5h 29mORD-PHL
12/10Tue
1 stopDelta
6h 54mPHL-ORD
$196
12/6Fri
nonstopUnited Airlines
2h 04mORD-PHL
12/15Sun
nonstopUnited Airlines
2h 24mPHL-ORD
$219

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Recent one-way flight deals

12/24Tue
nonstopFrontier
2h 03mMDW-PHL
$28
12/25Wed
nonstopFrontier
2h 07mORD-PHL
$28
1/7Tue
nonstopAmerican Airlines
2h 01mORD-PHL
$69
12/18Wed
nonstopSouthwest
1h 55mMDW-PHL
$69
12/4Wed
nonstopUnited Airlines
2h 00mORD-PHL
$86
12/24Tue
nonstopUnited Airlines
2h 06mORD-PHL
$89
12/25Wed
nonstopSouthwest
1h 55mMDW-PHL
$89
12/14Sat
1 stopDelta
4h 29mMDW-PHL
$98
12/15Sun
nonstopAmerican Airlines
2h 00mORD-PHL
$99
12/13Fri
1 stopDelta
6h 57mMDW-PHL
$118

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Last minute flights from Chicago to Wilmington

Last minute flight, train and bus deals

11/25Mon
nonstopFrontier
2h 02mMDW-PHL
12/17Tue
nonstopFrontier
2h 26mPHL-MDW
$107
11/25Mon
nonstopFrontier
2h 02mMDW-PHL
11/28Thu
nonstopFrontier
2h 23mPHL-MDW
$126
11/25Mon
nonstopFrontier
1h 58mMDW-PHL
12/6Fri
nonstopFrontier
2h 23mPHL-MDW
$127
11/25Mon
multi-stopDelta
7h 09mMDW-PHL
12/4Wed
multi-stopDelta
5h 20mPHL-MDW
$265
11/25Mon
multi-stopDelta
5h 29mORD-PHL
12/4Wed
multi-stopDelta
5h 38mPHL-ORD
$265
11/25Mon
multi-stopAmerican Airlines
4h 21mORD-PHL
12/8Sun
nonstopAmerican Airlines
2h 29mPHL-ORD
$296
11/25Mon
nonstopUnited Airlines
2h 00mORD-PHL
12/5Thu
nonstopUnited Airlines
2h 24mPHL-ORD
$313
11/25Mon
multi-stopSouthwest
11h 30mORD-PHL
12/8Sun
multi-stopSouthwest
8h 45mPHL-ORD
$335
11/25Mon
nonstopAmerican Airlines
1h 56mORD-PHL
12/2Mon
nonstopAmerican Airlines
2h 33mPHL-ORD
$366
11/22Fri
nonstopSouthwest
1h 55mMDW-PHL
12/4Wed
nonstopSouthwest
2h 10mPHL-MDW
$500

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