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Find cheap flights from Chicago to Wilmington from $39

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 5/31. 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.
1 adult
0 bags
Sat 6/15
Sat 6/22

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Good to know

Low season

January

High season

May

Cheapest flight

$39
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 5% 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 57m.

  • How many flights are there between Chicago and Wilmington?

    64 direct flights run between Chicago and Wilmington on a daily basis. On average, there are about 448 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 Sundays and the most expensive ones on Thursdays.

  • 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 $39. Frontier offered a round-trip connection from $55 and Spirit Airlines from $98.

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 78 days before departure, on average.
  • Book at least 2 weeks 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 October.
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
DeltaOverall score based on 10673 reviews
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Book cheap flights from Chicago to Wilmington

Recent round-trip flight deals

6/1Sat
nonstopFrontier
2h 01mMDW-PHL
6/4Tue
nonstopFrontier
2h 21mPHL-MDW
$55
5/29Wed
nonstopFrontier
2h 03mMDW-PHL
6/4Tue
nonstopFrontier
2h 21mPHL-MDW
$58
6/4Tue
1 stopSpirit Airlines
13h 20mORD-PHL
6/11Tue
2 stopsSpirit Airlines
25h 23mPHL-ORD
$98
5/28Tue
1 stopSpirit Airlines
9h 39mORD-PHL
5/29Wed
2 stopsSpirit Airlines
9h 50mPHL-ORD
$107
5/25Sat
nonstopAmerican Airlines
1h 57mORD-PHL
5/27Mon
nonstopAmerican Airlines
2h 23mPHL-ORD
$131
5/25Sat
1 stopUnited Airlines
5h 42mORD-PHL
5/27Mon
nonstopUnited Airlines
2h 24mPHL-ORD
$155
5/28Tue
nonstopAmerican Airlines
1h 57mORD-PHL
6/1Sat
nonstopAmerican Airlines
2h 33mPHL-ORD
$156
6/1Sat
1 stopDelta
4h 17mMDW-PHL
6/5Wed
1 stopDelta
4h 06mPHL-MDW
$176
5/25Sat
1 stopDelta
7h 17mORD-PHL
5/28Tue
1 stopDelta
6h 05mPHL-ORD
$176
5/20Mon
nonstopUnited Airlines
2h 03mORD-PHL
5/22Wed
nonstopUnited Airlines
2h 25mPHL-ORD
$206

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Recent one-way flight deals

5/31Fri
nonstopFrontier
2h 01mMDW-PHL
$39
6/7Fri
nonstopFrontier
2h 02mORD-PHL
$39
6/11Tue
1 stopSpirit Airlines
9h 29mORD-PHL
$41
6/18Tue
1 stopSpirit Airlines
9h 29mORD-PHL
$46
7/5Fri
nonstopAmerican Airlines
1h 57mORD-PHL
$59
5/28Tue
nonstopUnited Airlines
2h 08mORD-PHL
$66
7/15Mon
1 stopDelta
5h 57mMDW-PHL
$88
5/25Sat
1 stopDelta
7h 17mORD-PHL
$88
5/28Tue
nonstopAmerican Airlines
2h 04mORD-PHL
$91
5/28Tue
nonstopUnited Airlines
2h 08mORD-PHL
$101

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Last minute flights from Chicago to Wilmington

Last minute flight, train and bus deals

5/21Tue
nonstop
2h 03mORD-PHL
5/22Wed
multi-stop
8h 12mPHL-ORD
$59
5/21Tue
nonstopFrontier
2h 03mORD-PHL
5/27Mon
nonstopFrontier
2h 22mPHL-ORD
$86
5/21Tue
multi-stopSpirit Airlines
6h 15mORD-PHL
5/21Tue
multi-stopSpirit Airlines
22h 57mPHL-ORD
$122
5/21Tue
multi-stopSpirit Airlines
13h 20mORD-PHL
5/30Thu
multi-stopSpirit Airlines
21h 22mPHL-ORD
$142
5/20Mon
nonstopUnited Airlines
2h 03mORD-PHL
5/22Wed
nonstopUnited Airlines
2h 25mPHL-ORD
$206
5/21Tue
nonstopUnited Airlines
2h 08mORD-PHL
5/21Tue
nonstopUnited Airlines
2h 25mPHL-ORD
$215
5/18Sat
nonstopAmerican Airlines
2h 04mORD-PHL
5/26Sun
nonstopAmerican Airlines
2h 26mPHL-ORD
$231
5/18Sat
multi-stopDelta
3h 46mORD-PHL
5/25Sat
multi-stopDelta
5h 03mPHL-ORD
$238
5/17Fri
multi-stopAmerican Airlines
3h 55mORD-PHL
5/23Thu
nonstopAmerican Airlines
2h 26mPHL-ORD
$241
5/18Sat
multi-stopDelta
4h 23mORD-PHL
5/26Sun
multi-stopDelta
3h 59mPHL-ORD
$250

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Flights to Wilmington