$57 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 5/29. 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 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.

Recent round-trip flight deals from Illinois to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Illinois to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southern / Mokulele Logo
5:40 am - 7:37 amUIN-ORD
1h 57mnonstop
Southern / Mokulele Logo
1:10 pm - 3:05 pmORD-UIN
1h 55mnonstop
$101Southern / Mokulele
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Wed, May 28 - Thu, May 29
Denver Air Connection Logo
7:00 am - 7:55 amDBQ-ORD
0h 55mnonstop
Denver Air Connection Logo
5:00 pm - 5:55 pmORD-DBQ
0h 55mnonstop
$118Denver Air Connection
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Wed, May 28 - Wed, Jun 4
United Airlines Logo
9:50 am - 10:58 amDEC-ORD
1h 08mnonstop
United Airlines Logo
4:42 pm - 5:50 pmORD-DEC
1h 08mnonstop
$159United Airlines
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Wed, May 14 - Sun, May 18
Frontier Logo
5:45 pm - 12:20 amSTL-ORD
6h 35m1 stop
Frontier Logo
5:03 pm - 11:37 pmORD-STL
6h 34m1 stop
$162Frontier
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Wed, May 28 - Wed, Jun 4
 Logo
12:15 pm - 7:40 amSTL-ORD
19h 25m1 stop
 Logo
5:03 pm - 11:37 pmORD-STL
6h 34m1 stop
Tue, May 27 - Tue, Jun 3
 Logo
12:15 pm - 7:40 amSTL-ORD
19h 25m1 stop
 Logo
5:01 am - 2:07 pmORD-STL
9h 06m1 stop
Thu, Jun 12 - Sat, Jun 14
United Airlines Logo
3:53 pm - 5:04 pmPIA-ORD
1h 11mnonstop
United Airlines Logo
3:35 pm - 4:42 pmORD-PIA
1h 07mnonstop
$179United Airlines
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Tue, Jun 3 - Mon, Jun 9
American Airlines Logo
5:05 pm - 6:13 pmPIA-ORD
1h 08mnonstop
American Airlines Logo
10:15 pm - 11:19 pmORD-PIA
1h 04mnonstop
$184American Airlines
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Tue, Jun 3 - Mon, Jun 9
American Airlines Logo
6:32 pm - 7:36 pmMLI-ORD
1h 04mnonstop
American Airlines Logo
5:06 pm - 6:02 pmORD-MLI
0h 56mnonstop
$184American Airlines
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Thu, May 15 - Sun, May 25
Frontier Logo
9:55 pm - 2:48 pmSTL-MDW
16h 53m1 stop
Frontier Logo
6:15 am - 9:05 pmMDW-STL
14h 50m1 stop
$191Frontier
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Thu, May 15 - Sun, May 18
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Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$57
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Quincy to Chicago

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.

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.
7.4
United AirlinesOverall score based on 8696 reviews
6.6Food
7.7Boarding
8.1Crew
7.3Comfort
7.1Entertainment
Airline reviews

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

10.0 ExcellentDr. Joseph, Apr 2025IAH - ORD
Read more United Airlines reviews

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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 fine. I just forgot how smaller planes have more dips and seats in high winds.

It’s the only flight connecting Marion to Chicago, I do appreciate that it was available!

The flight was delayed and then less than 30 mins before boarding they cancelled the flight when clearly they had to have known earlier that they were going to have to cancel. There was only one person there available to talk to and all he could do was tell us to call reservations our self. Due to high call volume I waited 2 hours to even get rebooked on a flight to a different city where I would still have to drive 1 hr to my destination, only option for me. While waiting to talk to reservations people were getting emails with new flight info and the flights were days out and sone even a week out. . I did not get compensated in anyway after having spent all day at the airpot, not even a food voucher. Very disappointed, terrible experience.

Information regarding the delayed flight could have been better, and the Contour airlines app needs some serious updates. But overall, the crew was great and the flight was uneventful.

The boarding procedure is as easy and the crew very friendly.

This is a great airline for what it is. You get 1 checked bag included per passenger and the space per seat is incredible. It’s an E135 aircraft that is configured to seat 50 people but they have removed 20 seats and only seat 30 so you have a ton of legroom. They are doing things right and have a great product for what it is. It’s not going to knock your socks off in experience overall but the plane, although dates, was nice and clean and the crew was great. The flights were on time and super efficient. Will travel them again. I am a frequent traveler on all the larger airlines and this was just as good as any regional carrier, if not better. I expect big things out of Contour in the years to come.

Not waiting on the tarmac for an hour and 20 minutes

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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