$59 Find Cheap Flights from Illinois to Chicago - Compare and Save

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 8/15. 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

Thu, Aug 6 - Tue, Aug 18
United Airlines Logo
6:45 pm - 7:53 pm
DEC
-
ORD
1h 08mnonstop
United Airlines Logo
4:45 pm - 5:59 pm
ORD
-
DEC
1h 14mnonstop
$149United Airlines
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
7:20 pm - 8:37 pm
DEC
-
ORD
1h 17mnonstop
United Airlines Logo
4:45 pm - 5:59 pm
ORD
-
DEC
1h 14mnonstop
$159United Airlines
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
7:50 am - 1:20 pm
STL
-
MDW
5h 30m
2 stops
Southwest Logo
10:05 am - 4:50 pm
MDW
-
STL
6h 45m
2 stops
$186Southwest
Thu, Dec 10 - Wed, Jan 13
Delta Logo
2:18 pm - 8:24 pm
STL
-
ORD
6h 06m
1 stop
Delta Logo
1:35 pm - 8:37 pm
ORD
-
STL
7h 02m
1 stop
$186Delta
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
8:25 am - 9:30 am
STL
-
MDW
1h 05mnonstop
Southwest Logo
6:35 am - 7:45 am
MDW
-
STL
1h 10mnonstop
$187Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
6:30 am - 1:08 pm
STL
-
ORD
6h 38m
1 stop
Delta Logo
1:59 pm - 8:42 pm
ORD
-
STL
6h 43m
1 stop
$188Delta
Wed, Aug 12 - Thu, Aug 13
American Airlines Logo
8:07 pm - 9:40 pm
STL
-
ORD
1h 33mnonstop
American Airlines Logo
11:00 pm - 12:14 am
ORD
-
STL
1h 14mnonstop
$196American Airlines
Sun, Aug 23 - Wed, Aug 26
Frontier Logo
6:17 pm - 7:53 am
STL
-
ORD
13h 36m
1 stop
Frontier Logo
1:59 pm - 5:22 pm
ORD
-
STL
27h 23m
1 stop
$197Frontier
Thu, Oct 29 - Mon, Nov 2
Frontier Logo
10:35 am - 7:44 pm
STL
-
ORD
9h 09m
1 stop
Frontier Logo
8:00 am - 9:40 am
ORD
-
STL
25h 40m
2 stops
$198Frontier
Thu, Sep 17 - Thu, Sep 24
American Airlines Logo
6:00 am - 7:19 am
PIA
-
ORD
1h 19mnonstop
American Airlines Logo
11:00 pm - 12:08 am
ORD
-
PIA
1h 08mnonstop
$239American Airlines
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Good to know

Low season

January

Cheapest flight

$59
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 16% lower on average.
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.
7.7
ContourOverall score based on 42 reviews
7.4Comfort
6.2Entertainment
6.9Food
8.0Crew
7.7Boarding
Airline reviews

I’ve flown Contour on 4 different flights in the last couple weeks and every one of the flights were significantly delayed. Like over 2 hours delayed. 3 of the 4 were due to maintenance and one was weather, which is beyond their control. If this continues, I will not fly them anymore. It makes me concerned that they don’t have great maintenance practices. The planes are very old and worn out and the interiors need improvement. I do like the amount of space you have between seats for legroom. They also started charging for bags recently, which I think the did when they partnered up with American Airlines as a codeshare partner. American is also a disaster of an airline so I wish they had some agreement with Delta. I am glad they offer a major airline parternership though. That is certainly giving people more opportunities. I won’t fly Contour unless they have a direct flight to where I am going. If I have to connect then I am going to take Delta. The bus at the DFW airport to get on and off the aircraft is a pain and adds so much extra time to your travel experience. I hope this is temporary while they are building a new terminal, but I don’t know.

6.0 GoodLane, Jun 2026
DFW - TUP
Read more Contour reviews

I’ve flown Contour on 4 different flights in the last couple weeks and every one of the flights were significantly delayed. Like over 2 hours delayed. 3 of the 4 were due to maintenance and one was weather, which is beyond their control. If this continues, I will not fly them anymore. It makes me concerned that they don’t have great maintenance practices. The planes are very old and worn out and the interiors need improvement. I do like the amount of space you have between seats for legroom. They also started charging for bags recently, which I think the did when they partnered up with American Airlines as a codeshare partner. American is also a disaster of an airline so I wish they had some agreement with Delta. I am glad they offer a major airline parternership though. That is certainly giving people more opportunities. I won’t fly Contour unless they have a direct flight to where I am going. If I have to connect then I am going to take Delta. The bus at the DFW airport to get on and off the aircraft is a pain and adds so much extra time to your travel experience. I hope this is temporary while they are building a new terminal, but I don’t know.

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!

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

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.

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

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

The head rest is too big and cannot be placed differently/removed. Causes one head to tilt forward and increase back pain

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

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

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

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.

The flight was delayed instead of leaving at 11 it left at 12.20

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

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
Schererville
Munster
Chesterton
Porter
Monticello
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Griffith

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.