$58 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 4/1. 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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Cheap Flight Deals from Chicago to Wilmington (CHI-PHL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Wilmington that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Wilmington

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Wilmington.
Discover the best prices for you by selecting your travel dates on KAYAK.
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8:52 pm - 11:56 pmMDW-PHL
2h 04mnonstop
6:35 pm - 7:52 pmPHL-MDW
2h 17mnonstop
$118Frontier
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Sat, Jun 7 - Sat, Jun 14
11:00 am - 5:57 pmORD-PHL
5h 57m1 stop
12:53 pm - 8:55 amPHL-ORD
21h 02m1 stop
$131Spirit Airlines
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Thu, May 8 - Sun, May 11
8:25 am - 11:25 amMDW-PHL
2h 00mnonstop
12:15 pm - 1:20 pmPHL-MDW
2h 05mnonstop
$157Southwest
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Tue, Apr 22 - Tue, Apr 29
11:10 am - 2:18 pmORD-PHL
2h 08mnonstop
6:41 am - 8:05 amPHL-ORD
2h 24mnonstop
$168United Airlines
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Sat, Apr 26 - Tue, Apr 29
7:30 am - 10:38 amORD-PHL
2h 08mnonstop
6:30 am - 7:54 amPHL-ORD
2h 24mnonstop
$177United Airlines
Find Deal
Wed, Apr 30 - Thu, May 1
8:25 am - 11:25 amMDW-PHL
2h 00mnonstop
2:40 pm - 3:45 pmPHL-MDW
2h 05mnonstop
$177Southwest
Find Deal
Wed, Apr 30 - Thu, May 1
10:20 am - 6:00 pmMDW-PHL
6h 40m1 stop
11:31 am - 5:19 pmPHL-MDW
6h 48m1 stop
$197Delta
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Tue, Apr 22 - Tue, Apr 29
8:48 pm - 11:59 pmORD-PHL
2h 11mnonstop
9:17 pm - 10:47 pmPHL-ORD
2h 30mnonstop
$198American Airlines
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Fri, May 2 - Sun, May 4
9:20 am - 3:49 pmMDW-PHL
5h 29m1 stop
4:57 pm - 9:27 pmPHL-MDW
5h 30m1 stop
$198Delta
Find Deal
Tue, May 20 - Wed, May 28
6:45 am - 9:48 amORD-PHL
2h 03mnonstop
9:17 pm - 10:47 pmPHL-ORD
2h 30mnonstop
$207American Airlines
Find Deal
Thu, May 1 - Sun, May 4

Good to know

Low season

January

High season

July

Cheapest flight

$58
Best time to beat the crowds but there is an average 53% increase in price.
Most popular time to fly and prices are also 22% 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?

    61 direct flights run between Chicago and Wilmington on a daily basis. On average, there are about 432 departures each week.

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

    Consider leaving on a Saturday and avoid Fridays 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 Wednesdays.

  • 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 $58. Frontier offered a round-trip connection from $118 and Spirit Airlines from $131.

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 83 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.
8.0
SouthwestOverall score based on 4272 reviews
8.0Comfort
8.6Crew
8.2Boarding
7.1Food
7.6Entertainment
Airline reviews

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

8.0 ExcellentCarolynn, Mar 2025SMF - KOA
Read more Southwest reviews

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

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.

They switched my flight to Spirit, Never using Kayak again,

i was denied boarding, even though i had an assigned seat, checked in on line and was at airport early. Then they refused to fully refund the the fair and replacement fair because they claimed it was "no show/denied boarding". I will never fly this airline again

I was not permitted on my flight and had to purchase another flight ticket to Las Vegas.

This was a full flight and I was in Zone 1, however upon boarding, several other zones went in ahead of me, leaving no overhead cabin space near my seat. This created a challenging disembarkment process.

Frontier had yet another flight cancellation. Have never made a complete round trip with this airline without at least one leg getting cancelled. Miserable flights - dirty, uncomfortable planes that apparently always have issues since I've had multiple delays and cancellations with them.

Flight was delayed 3 times, would have been nice to have received text message instead of email notifications. Frontier app wasn’t even updated accordingly, no gate number disclosed. No agent at front desk of gate to inform of delay. Very confused and left if the dark

It was a no frills flight. Would have liked to be able to charge my device

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Asked for a seat change to be w my wife at the gate they were great in sorting it out to make it happen

Everything went as planned. Crew was great. Seats were still not that comfortable.

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

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