$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 4/5. 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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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

Sun, Apr 5 - Thu, Apr 9
Contour Logo
4:40 pm - 6:05 pm
BRL
-
ORD
1h 25mnonstop
Contour Logo
6:45 pm - 8:05 pm
ORD
-
BRL
1h 20mnonstop
$81Contour
Sat, Apr 4 - Wed, Apr 8
Contour Logo
9:10 am - 10:35 am
BRL
-
ORD
1h 25mnonstop
Contour Logo
12:00 pm - 1:20 pm
ORD
-
BRL
1h 20mnonstop
$82Contour
Sat, May 2 - Thu, May 7
Multiple Airlines Logo
8:23 pm - 10:23 am
STL
-
ORD
14h 00m
1 stop
Multiple Airlines Logo
11:51 am - 4:54 pm
ORD
-
STL
5h 03m
1 stop
$172Multiple Airlines
Tue, Apr 7 - Thu, Apr 9
Southwest Logo
8:30 am - 3:05 pm
STL
-
MDW
6h 35m
1 stop
Southwest Logo
7:40 am - 1:45 pm
MDW
-
STL
6h 05m
1 stop
$174Southwest
Wed, Apr 8 - Sat, Apr 11
Southwest Logo
5:45 am - 11:10 am
STL
-
ORD
5h 25m
1 stop
Southwest Logo
2:05 pm - 8:20 pm
ORD
-
STL
6h 15m
1 stop
$174Southwest
Sat, Apr 18 - Sat, Apr 25
United Airlines Logo
9:16 am - 10:45 am
STL
-
ORD
1h 29mnonstop
United Airlines Logo
9:15 am - 10:45 am
ORD
-
STL
1h 30mnonstop
$191United Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
7:05 am - 8:36 am
STL
-
ORD
1h 31mnonstop
American Airlines Logo
10:30 pm - 11:46 pm
ORD
-
STL
1h 16mnonstop
$192American Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
5:51 am - 7:21 am
STL
-
ORD
1h 30mnonstop
American Airlines Logo
10:30 pm - 11:46 pm
ORD
-
STL
1h 16mnonstop
$193American Airlines
Wed, Apr 1 - Sun, Apr 5
United Airlines Logo
5:00 am - 6:43 am
PAH
-
ORD
1h 43mnonstop
United Airlines Logo
12:07 pm - 1:35 pm
ORD
-
PAH
1h 28mnonstop
$194United Airlines
Wed, Apr 15 - Fri, Apr 24
Multiple Airlines Logo
10:06 am - 3:08 pm
SPI
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
2:09 pm - 9:26 am
ORD
-
SPI
19h 17m
2 stops
$302Multiple Airlines
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Good to know

Low seasonJanuary
Cheapest flight$42
Best time to beat the crowds but there is an average 55% increase in price.
Flight from Burlington 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
6.8Food
7.3Comfort
7.6Boarding
6.1Entertainment
7.9Crew
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.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

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.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

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.

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
Schererville
Munster
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.