$49 Find Cheap Flights from Illinois to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 2/20. 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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1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Illinois to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Illinois to Chicago 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Illinois to Chicago

Mon, Nov 24 - Thu, Nov 27
Southwest Logo
2:30 pm - 3:40 pmSTL-MDW
1h 10mnonstop
Southwest Logo
9:30 am - 10:45 amMDW-STL
1h 15mnonstop
$97Southwest
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Mon, Nov 24 - Thu, Nov 27
American Airlines Logo
7:58 pm - 9:29 pmSTL-ORD
1h 31mnonstop
American Airlines Logo
3:00 pm - 4:25 pmORD-STL
1h 25mnonstop
$97American Airlines
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Tue, Dec 2 - Tue, Dec 9
Contour Logo
9:50 am - 11:10 amUIN-ORD
1h 20mnonstop
Contour Logo
2:00 pm - 3:20 pmORD-UIN
1h 20mnonstop
$104Contour
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Mon, Dec 1 - Mon, Dec 8
Contour Logo
9:50 am - 11:10 amUIN-ORD
1h 20mnonstop
Contour Logo
2:00 pm - 3:20 pmORD-UIN
1h 20mnonstop
$105Contour
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Thu, Dec 4 - Mon, Dec 8
Frontier Logo
12:04 pm - 10:12 pmSTL-MDW
10h 08m1 stop
Frontier Logo
3:10 pm - 10:33 pmMDW-STL
7h 23m1 stop
$110Frontier
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Mon, Nov 17 - Wed, Nov 19
Frontier Logo
12:09 pm - 12:49 amSTL-ORD
12h 40m1 stop
Frontier Logo
12:37 pm - 11:01 pmORD-STL
10h 24m1 stop
$110Frontier
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Tue, Jan 13 - Wed, Jan 14
United Airlines Logo
8:05 am - 9:40 amSTL-ORD
1h 35mnonstop
United Airlines Logo
7:40 pm - 9:13 pmORD-STL
1h 33mnonstop
$117United Airlines
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Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
7:05 pm - 8:15 pmDEC-ORD
1h 10mnonstop
United Airlines Logo
7:45 am - 8:52 amORD-DEC
1h 07mnonstop
$149United Airlines
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Mon, Nov 24 - Thu, Nov 27
Delta Logo
6:00 am - 11:52 amSTL-MDW
5h 52m1 stop
Delta Logo
5:34 pm - 9:58 pmMDW-STL
4h 24m1 stop
$157Delta
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Tue, Feb 24 - Wed, Feb 25
Delta Logo
7:10 am - 1:39 pmSTL-ORD
6h 29m1 stop
Delta Logo
2:03 pm - 8:45 pmORD-STL
6h 42m1 stop
$157Delta
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Everything you should know

Cheapest round-trip
$97
Overall average: $256
Southwest
Mon 11/24Thu 11/27
STL - MDW • Non-stop
Cheapest one-way
$49
Southwest
Fri 2/20
STL - MDW • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from St. Louis to Chicago Midway Airport

FAQs for booking flights from Illinois to Chicago

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

    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 Illinois to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Illinois 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 Illinois to Chicago?

    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 Chicago with an airline and back to Illinois with another airline.

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

    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 Chicago from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Illinois to Chicago

 
Need help choosing which airline to fly with from Illinois to Chicago? 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.
7.5
ContourOverall score based on 40 reviews
7.5Boarding
6.4Entertainment
7.3Comfort
6.9Food
7.9Crew
Airline reviews

All the staff were amazing! The flight was quick, everything went smoothly, I have nothing but good things to say about this flight. Thank you Contour!

10.0 ExcellentJustin, Oct 2025PBG - IAD
Read more Contour reviews

All the staff were amazing! The flight was quick, everything went smoothly, I have nothing but good things to say about this flight. Thank you Contour!

It was easy, efficient from start to finish. The flight attendant was amazing. Smooth ride. It was just perfect.

We had a great experience on both of our flights! Crew was great…..the ride was smooth…and checking in was easy. We will definitely fly with them again.

This was my first time flying with Contour and the Greenbrier Valley Airport. It both were excellent and the price couldn’t be beat!

Not on time. Taxied around the airport for 30 MINUTES! The pilot never said a word. Ai

Great flight, professional crew, convenient and interesting nonstop routes. Had trouble with getting precheck listed on boarding pass, but found that customer service was remarkably responsive via email — unheard of with other carriers. A great experience overalll.

I felt like a sardine in my seat. We all did. The plane was so small that I hit my head on the roof when I stood up from my seat. The service was good and the crew were nice.

My luggage is missing and contour is doing a terrible service helping finding it. Unbelievable and the worst experience ever. I would love get my money back.

Flight was cancelled, but they got him on an earlier delayed rescheduled one. Arrived Chicago 2 hours later than expected but long layover so it worked.

Crew very helpful, weather made the flight less than optimal.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint Joseph
Hammond
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Chesterton
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Munster
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Monticello
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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Illinois

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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