$39 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Wilmington.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:59 pm - 12:58 amMDW-PHL
1h 59mnonstop
6:03 pm - 11:29 pmPHL-MDW
6h 26m1 stop
$98Frontier
Find Deal
Mon, Jan 6 - Sat, Jan 11
9:59 pm - 12:58 amMDW-PHL
1h 59mnonstop
6:03 pm - 11:29 pmPHL-MDW
6h 26m1 stop
$99Frontier
Find Deal
Mon, Jan 6 - Sat, Jan 11
2:29 pm - 5:35 pmORD-PHL
2h 06mnonstop
10:10 am - 11:41 amPHL-ORD
2h 31mnonstop
$181United Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:28 pm - 11:20 pmMDW-PHL
3h 52m1 stop
6:00 am - 12:46 pmPHL-MDW
7h 46m1 stop
$200Delta
Find Deal
Tue, Jan 7 - Wed, Jan 15
5:45 am - 12:04 pmORD-PHL
5h 19m1 stop
9:33 am - 12:55 pmPHL-ORD
4h 22m1 stop
$200Delta
Find Deal
Tue, Jan 7 - Wed, Jan 15
6:30 pm - 9:40 pmORD-PHL
2h 10mnonstop
12:15 pm - 1:47 pmPHL-ORD
2h 32mnonstop
$201United Airlines
Find Deal
Tue, Jan 14 - Thu, Jan 16
10:05 am - 1:00 pmMDW-PHL
1h 55mnonstop
1:50 pm - 3:05 pmPHL-MDW
2h 15mnonstop
$202Southwest
Find Deal
Mon, Jan 13 - Tue, Jan 14
3:15 pm - 9:45 pmMDW-PHL
5h 30m1 stop
1:30 pm - 2:45 pmPHL-MDW
2h 15mnonstop
$211Southwest
Find Deal
Tue, Jan 14 - Thu, Jan 16
8:05 am - 12:50 pmORD-PHL
3h 45m1 stop
3:55 pm - 5:24 pmPHL-ORD
2h 29mnonstop
$226American Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
9:45 am - 12:49 pmORD-PHL
2h 04mnonstop
5:54 pm - 9:42 pmPHL-ORD
4h 48m1 stop
$228American Airlines
Find Deal
Tue, Jan 14 - Mon, Jan 20

Good to know

Low season

January

High season

July

Cheapest flight

$39
Best time to beat the crowds but there is an average 29% 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 50m.

  • How many flights are there between Chicago and Wilmington?

    52 direct flights run between Chicago and Wilmington on a daily basis. On average, there are about 365 departures each week.

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

    Consider leaving on a Monday and avoid Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays 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 $98 and Spirit Airlines from $156.

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 4848 reviews
7.2Food
8.7Crew
8.2Boarding
8.1Comfort
7.7Entertainment
Airline reviews

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

10.0 ExcellentRoxann, Dec 2024MCO - STL
Read more Southwest reviews

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Everything was great. Great service, excellent communication, and early arrival

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

It was terrible, if they ran flights on time it would make a big difference.

Great flight. On-time, comfortable, clean aircraft, and offered snacks pre-flight to plan for a potentially turbulent route. I wish there was Wi-Fi an all Delta Aircrafts but for a short flight this is not much of a problem.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

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

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

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

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.

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.

A lady asked to stop the flight after the tunnel pulled away and we began to depart a flight that was already hours late. The attendance respectfully stopped the the plane and had the tunnel return. After the tunnel returned the passenger claimed to have changed her mind . The tunnel was then put in reverse and the passenger remained on the plane .. They should have sent the sick passenger off the plane like initially replaced. They existed a couple off the plane prior to that situation.. So.. all and all.. it was a long and flight.. .

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

I ended up paying $70+ dollars to for a carryon because the website is confusing and misleading. I now realize I did not need to pay that. I request a refund. I will pay extra to other airlines and not fly Frontier again.

With frontier you get what you pay for. The flight was two hours late. It’s a tight fit for the number of people they bring but you get to where you’re going cheap. Sometimes that’s more important than a nifty drink and cool TV..

Charges unexpected. For seat that didnt recline. Please reverse extra seat and carryon charge. Bad business that is a bait and switch.

Although we received an email from Kayak AND the airline, turns out we were not on Frontier’s manifest for the flight. We had to purchase tickets at the gate. Not sure where this transaction fell apart, but it did. We are now disputing the charges for the SLC to PDX flight originally booked through Kayak.

We had an awful experience getting our bags checked in. Frontier’s check in on the app manipulated us into buying the business package because that was the only option available for a checked bag which included two checked bags per person which we did not need. Upon arriving to the airport, we stood in line for what seemed like forever at the baggage check in and there was no one available at the counter. We were first in line and we were afraid we were going to miss our flight due to the baggage attendant being late. After realizing there were a lot of other people waiting at the baggage check in and no one available. I reached out to Frontier and could not get any customer service so I had to call the airport to page the baggage attendant to send someone to the counter to check in our bags before we were able to go through security , I finally spoke to the attendant at the counter and explained to her that we had to pay for two checked bags person a total of six bags when we only had a total of three bags between three people she said to reach out to Frontier and they would issue a refund for the three bags that we paid for and did not need. I reached out to Frontier which I was not able to reach anybody by phone so I had to go through their automated chat feature, which sent me around in circles until I finally reached a representative to assist me. I explained to them what happened and they explained that they were not able to assist me. I continued to push the issue with them as this was very frustrating and they finally put in a customer service ticket where we were issued a flight credit and we were so disappointed because after this experience, we NEVER want to fly Frontier again, and we do not want a credit that we will not use. Frontier charged us almost $500 for us to check three bags which is absolutely absurd! The customer service agents were not able to offer anything else other than a flight credit and I do not feel like my frustrations were truly heard , we will never use Frontier Airlines again ! Truly Theft by Manipulation! They should be ashamed!

I couldn’t check in because the app didn’t work. It took 3 Frontier employees at the counter to get me checked in. Flight left 3 hours after departure time

One crew member was rude about our bags. Be nice about it. We don’t fly a lot. And the fact that you have to pay for a carry on is ridiculous

While booking it was not obvious that I had to pay for carryon. Realized it only during check-in. Overall, meh!

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