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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, Nov 5 - Mon, Nov 9
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$101Contour
Sun, Nov 8 - Thu, Nov 12
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$101Contour
Mon, Nov 23 - Mon, Nov 30
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$102Contour
Sat, Nov 7 - Sun, Nov 8
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
6:59 am - 8:09 amORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Wed, Nov 4 - Sun, Nov 8
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
6:59 am - 8:09 amORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Tue, Nov 24 - Fri, Nov 27
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
5:00 pm - 6:10 pmORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Mon, Nov 9 - Fri, Nov 13
2:40 pm - 11:13 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
32h 33m2 stops Nashville Intl Dallas/Fort Worth
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$251Multiple Airlines
Sat, Dec 5 - Sat, Dec 12
10:21 am - 12:14 pmMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 53mnonstop
11:00 pm - 12:36 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Sat, Dec 5 - Sat, Dec 12
10:21 am - 12:14 pmMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 53mnonstop
8:15 am - 9:51 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Mon, Nov 23 - Mon, Nov 30
2:40 pm - 7:47 amUIN Quincy Regional-ORD Chicago O'Hare Intl
17h 07m2 stops Nashville Intl Dallas/Fort Worth
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$262Multiple Airlines
Recent one-way flight deals from Illinois to Chicago
Thu, Nov 19
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
$50Contour
Thu, Nov 5
9:10 am - 10:19 amDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 09mnonstop
$98United Airlines
Fri, Nov 20
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
$98United Airlines
Sat, Nov 28
9:15 am - 10:24 amDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 09mnonstop
$98United Airlines
Wed, Nov 25
2:33 pm - 3:47 pmBMI Bloomington-Normal-ORD Chicago O'Hare Intl
1h 14mnonstop
$141American Airlines
Sun, Nov 22
9:29 pm - 5:10 amPIA Greater Peoria-ORD Chicago O'Hare Intl
31h 41m1 stop Las Vegas Harry Reid Intl
$173Multiple Airlines
Sun, Nov 22
9:29 pm - 7:47 amPIA Greater Peoria-ORD Chicago O'Hare Intl
34h 18m2 stops Las Vegas Harry Reid Intl Dallas/Fort Worth
$179Multiple Airlines
Thu, Nov 19
2:40 pm - 12:43 amUIN Quincy Regional-ORD Chicago O'Hare Intl
34h 03m2 stops Nashville Intl Orlando
$209Multiple Airlines
Wed, Nov 11
11:20 am - 12:36 pmMLI Moline Quad-City-ORD Chicago O'Hare Intl
1h 16mnonstop
$269American Airlines
Mon, Dec 7
5:14 pm - 6:30 pmMLI Moline Quad-City-ORD Chicago O'Hare Intl
1h 16mnonstop
$269American Airlines
Recent last minute flight deals from Illinois to Chicago
Thu, Oct 29 - Thu, Nov 5
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$171Contour
Fri, Oct 30 - Fri, Nov 6
9:10 am - 10:19 amDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 09mnonstop
5:00 pm - 6:10 pmORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$199United Airlines
Fri, Oct 30 - Fri, Oct 30
9:10 am - 10:19 amDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 09mnonstop
4:45 pm - 5:55 pmORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$291United Airlines
Tue, Oct 27 - Thu, Oct 29
7:02 pm - 8:30 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
4:45 pm - 5:55 pmORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$291United Airlines
Fri, Oct 30 - Sun, Nov 1
6:00 am - 7:19 amMLI Moline Quad-City-ORD Chicago O'Hare Intl
1h 19mnonstop
3:17 pm - 4:28 pmORD Chicago O'Hare Intl-MLI Moline Quad-City
1h 11mnonstop
$369American Airlines
Fri, Oct 30 - Sat, Oct 31
6:00 am - 7:19 amMLI Moline Quad-City-ORD Chicago O'Hare Intl
1h 19mnonstop
3:17 pm - 4:32 pmORD Chicago O'Hare Intl-MLI Moline Quad-City
1h 15mnonstop
$369American Airlines
Thu, Oct 29 - Wed, Nov 4
10:48 am - 12:24 pmMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 36mnonstop
11:00 pm - 12:27 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 27mnonstop
$395American Airlines
Thu, Oct 29 - Thu, Nov 5
2:40 pm - 10:43 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
8h 03m2 stops Nashville Intl Philadelphia
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$427Multiple Airlines
Thu, Oct 29 - Thu, Nov 5
2:40 pm - 12:51 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
46h 11m3 stops Nashville Intl Orlando Sanford Intl Atlanta Hartsfield-Jackson
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$473Multiple Airlines
Sat, Oct 31 - Sat, Nov 7
11:29 am - 1:21 amMLI Moline Quad-City-ORD Chicago O'Hare Intl
37h 52m2 stops Tampa St. Petersburg Denver Intl
4:00 pm - 9:59 amORD Chicago O'Hare Intl-MLI Moline Quad-City
17h 59m1 stop Orlando
$555Multiple Airlines
Recent direct flight deals from Illinois to Chicago
Sun, Nov 8 - Thu, Nov 12
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$101Contour
Thu, Nov 5 - Mon, Nov 9
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$101Contour
Mon, Nov 23 - Mon, Nov 30
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$102Contour
Wed, Nov 4 - Sun, Nov 8
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$102Contour
Sat, Nov 7 - Sun, Nov 8
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
6:59 am - 8:09 amORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Wed, Nov 4 - Sun, Nov 8
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
6:59 am - 8:09 amORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Tue, Nov 24 - Fri, Nov 27
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
5:00 pm - 6:10 pmORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Sat, Dec 5 - Sat, Dec 12
10:21 am - 12:14 pmMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 53mnonstop
11:00 pm - 12:36 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Sat, Dec 5 - Sat, Dec 12
10:21 am - 12:14 pmMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 53mnonstop
8:15 am - 9:51 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Wed, Dec 23 - Fri, Jan 8
5:00 am - 6:45 amMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 45mnonstop
10:30 pm - 12:11 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 41mnonstop
$282American Airlines
Useful Info
Good to know
Low season | February |
|---|---|
High season | April |
Cheapest flight | $50 |
FAQs for booking flights from Illinois to Chicago
Reviews of the top 3 airlines serving from Illinois to Chicago
7.5
ContourOverall score based on 43 reviews
7.5Boarding
6.8Food
6.1Entertainment
7.8Crew
7.3Comfort
Airline reviews
You could have NOT left me and my family high and dry by not completing the reservation changes because they no longer have the contract from Phoenix AZ to Moab Utah. There wasn't even a ticket agent for Contour in Phoenix to talk to. Cost my an additional $1600. to rent a vehicle to get my family to Utah. Now I'm left with trying to have someone make it right financially. I'm not optimistic..........
2.0 MediocreBarbra, Aug 2026
You could have NOT left me and my family high and dry by not completing the reservation changes because they no longer have the contract from Phoenix AZ to Moab Utah. There wasn't even a ticket agent for Contour in Phoenix to talk to. Cost my an additional $1600. to rent a vehicle to get my family to Utah. Now I'm left with trying to have someone make it right financially. I'm not optimistic..........
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.
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!
Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol
It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.
Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.
The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.
The first leg of my trip the Republic Airlines aircraft was late due to a maintenance problem. Then I called United to reroute. Their reroute airline lost my bag but found it and returned it two days later. Hopefully my return trip home is better.
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
The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.
The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.
No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.
Same the delay was not ideal and the credits to move flights was not sufficient
No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.
The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.
first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!
Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.
12 hour wait in pdx to my initial flight to Dallas to hunstville
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 locationsMerrillville
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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.
First Class flights to Chicagofrom $471
Business Class flights to Chicagofrom $471
Economy Class flights to Chicagofrom $102
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Flights from domestic origins to Chicago
Flights from all regions of Illinois to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
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Flights to Chicago Midway Airportfrom $117
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.