$42 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 6/14. 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
1 adult, Economy, 0 bags

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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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Illinois to Chicago

Sat, Apr 4 - Sat, Apr 18
Contour Logo
9:45 am - 11:20 am
UIN
-
ORD
1h 35mnonstop
Contour Logo
2:45 pm - 4:05 pm
ORD
-
UIN
1h 20mnonstop
$86Contour
Fri, Mar 20 - Sun, Mar 29
Contour Logo
8:45 am - 10:10 am
BRL
-
ORD
1h 25mnonstop
Contour Logo
12:00 pm - 1:20 pm
ORD
-
BRL
1h 20mnonstop
$86Contour
Sat, Mar 7 - Wed, Mar 11
United Airlines Logo
7:15 pm - 8:25 pm
DEC
-
ORD
1h 10mnonstop
United Airlines Logo
7:45 am - 8:52 am
ORD
-
DEC
1h 07mnonstop
$149United Airlines
Sat, Mar 28 - Sun, Apr 5
United Airlines Logo
7:15 pm - 8:25 pm
DEC
-
ORD
1h 10mnonstop
United Airlines Logo
7:45 am - 8:58 am
ORD
-
DEC
1h 13mnonstop
$159United Airlines
Sat, Mar 21 - Fri, Mar 27
American Airlines Logo
12:48 pm - 1:54 pm
PIA
-
ORD
1h 06mnonstop
American Airlines Logo
10:24 pm - 11:25 pm
ORD
-
PIA
1h 01mnonstop
$179American Airlines
Tue, Apr 7 - Wed, Apr 29
American Airlines Logo
5:15 am - 6:33 am
MLI
-
ORD
1h 18mnonstop
American Airlines Logo
4:54 pm - 6:07 pm
ORD
-
MLI
1h 13mnonstop
$179American Airlines
Thu, Mar 12 - Fri, Mar 13
Southwest Logo
9:50 pm - 11:00 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
2:35 pm - 3:50 pm
MDW
-
STL
1h 15mnonstop
$196Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
3:55 pm - 5:05 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
8:15 am - 9:30 am
MDW
-
STL
1h 15mnonstop
$201Southwest
Thu, Mar 26 - Mon, Mar 30
Frontier Logo
11:21 am - 7:47 pm
STL
-
MDW
8h 26m
1 stop
Frontier Logo
6:00 am - 10:32 am
MDW
-
STL
28h 32m
1 stop
$202Frontier
Tue, Mar 24 - Tue, Mar 31
Frontier Logo
11:27 am - 6:47 pm
STL
-
ORD
7h 20m
1 stop
Frontier Logo
8:55 pm - 9:48 am
ORD
-
STL
12h 53m
2 stops
$202Frontier
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$42
Best time to beat the crowds but there is an average 55% increase in price.
Most popular time to fly with an average 2% increase in price.
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.

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.
7.6
ContourOverall score based on 42 reviews
7.9Crew
6.1Entertainment
6.8Food
7.3Comfort
7.6Boarding
Airline reviews

Short flight so no entertainment and none expected or appropriate. Everyone I dealt with was professional and helpful. A good experience.

10.0 ExcellentAnonymous, Nov 2025
TSM - DEN
Read more Contour reviews

Short flight so no entertainment and none expected or appropriate. Everyone I dealt with was professional and helpful. A good experience.

Love it. No Frills but better than Spirit No Frills. It's like a simple luxury private plane especially if you've got five or six people on it because then you probably got your own section of the plane.

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.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Munster
Schererville
Porter
Monticello
Griffith
Saint John

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.