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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
Tue, Dec 1 - Tue, Dec 8
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$112Contour
Thu, Jan 14 - Sun, Jan 17
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
$121Contour
Mon, Jan 11 - Mon, Jan 18
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
$124Contour
Sat, Nov 28 - Sun, Nov 29
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
Fri, Nov 27 - Sun, Nov 29
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 18 - Sun, Nov 22
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
Wed, Dec 2 - Tue, Dec 8
6:39 am - 8:35 amMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 56mnonstop
11:00 pm - 12:36 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Sat, Nov 21 - Sun, Nov 22
7:01 pm - 8:30 pmCMI Champaign University-Willard-ORD Chicago O'Hare Intl
1h 29mnonstop
7:10 pm - 8:18 pmORD Chicago O'Hare Intl-CMI Champaign University-Willard
1h 08mnonstop
$271American Airlines
Tue, Dec 1 - Tue, Dec 8
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
7:25 am - 9:25 amORD Chicago O'Hare Intl-UIN Quincy Regional
50h 00m2 stops Denver Intl Nashville Intl
$271Multiple Airlines
Mon, Jan 11 - Mon, Jan 18
2:40 pm - 12:26 amUIN Quincy Regional-ORD Chicago O'Hare Intl
33h 46m2 stops Nashville Intl Denver Intl
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$284Multiple Airlines
Recent one-way flight deals from Illinois to Chicago
Fri, Dec 4
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
$49Contour
Wed, Nov 18
9:55 am - 11:40 amUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
$49Contour
Tue, Dec 15
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
$59Contour
Sat, Nov 14
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
$98United Airlines
Fri, Nov 20
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
$98United Airlines
Fri, Jan 1
7:03 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 22mnonstop
$98United Airlines
Sat, Nov 21
5:00 am - 6:11 amBMI Bloomington-Normal-ORD Chicago O'Hare Intl
1h 11mnonstop
$146American Airlines
Sun, Dec 20
5:00 am - 6:45 amMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 45mnonstop
$149American Airlines
Sun, Nov 22
9:20 pm - 5:10 amMLI Moline Quad-City-ORD Chicago O'Hare Intl
31h 50m1 stop Las Vegas Harry Reid Intl
$175Multiple Airlines
Fri, Dec 4
2:40 pm - 12:54 amUIN Quincy Regional-ORD Chicago O'Hare Intl
34h 14m2 stops Nashville Intl Denver Intl
$195Multiple Airlines
Recent last minute flight deals from Illinois to Chicago
Sat, Nov 7 - Wed, Nov 11
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$183Contour
Mon, Nov 9 - Fri, Nov 13
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
$188Contour
Sat, Nov 7 - Wed, Nov 11
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$193Contour
Sun, Nov 8 - Sun, Nov 15
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
$199United Airlines
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
$199United Airlines
Sun, Nov 8 - Tue, Dec 8
6:45 am - 8:35 amMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 50mnonstop
11:00 pm - 12:36 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$341American Airlines
Sat, Nov 7 - Sat, Nov 14
8:13 am - 9:30 amMLI Moline Quad-City-ORD Chicago O'Hare Intl
1h 17mnonstop
8:05 pm - 9:22 pmORD Chicago O'Hare Intl-MLI Moline Quad-City
1h 17mnonstop
$354United Airlines
Fri, Nov 6 - Tue, Nov 10
6:00 am - 7:25 amMLI Moline Quad-City-ORD Chicago O'Hare Intl
1h 25mnonstop
9:40 am - 10:50 amORD Chicago O'Hare Intl-MLI Moline Quad-City
1h 10mnonstop
$369American Airlines
Sat, Nov 7 - Wed, Nov 11
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
6:30 am - 9:25 amORD Chicago O'Hare Intl-UIN Quincy Regional
26h 55m2 stops Denver Intl Nashville Intl
$412Multiple Airlines
Sat, Nov 7 - Wed, Nov 11
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
6:30 am - 9:25 amORD Chicago O'Hare Intl-UIN Quincy Regional
26h 55m2 stops Denver Intl Nashville Intl
$423Multiple Airlines
Recent direct flight deals from Illinois to Chicago
Tue, Dec 1 - Tue, Dec 8
3:35 pm - 5:20 pmUIN Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
12:15 pm - 1:40 pmORD Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$112Contour
Thu, Jan 14 - Sun, Jan 17
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
$121Contour
Mon, Jan 11 - Mon, Jan 18
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
$124Contour
Sat, Nov 28 - Sun, Nov 29
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
Fri, Nov 27 - Sun, Nov 29
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 18 - Sun, Nov 22
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
Fri, Dec 11 - Sun, Dec 13
6:57 pm - 8:25 pmDEC Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
4:59 pm - 6:09 pmORD Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$159United Airlines
Wed, Dec 2 - Tue, Dec 8
6:39 am - 8:35 amMWA Marion Williamson County-ORD Chicago O'Hare Intl
1h 56mnonstop
11:00 pm - 12:36 amORD Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Sat, Nov 21 - Sun, Nov 22
7:01 pm - 8:30 pmCMI Champaign University-Willard-ORD Chicago O'Hare Intl
1h 29mnonstop
7:10 pm - 8:18 pmORD Chicago O'Hare Intl-CMI Champaign University-Willard
1h 08mnonstop
$271American Airlines
Sun, Nov 22 - Tue, Nov 24
5:53 am - 7:16 amCMI Champaign University-Willard-ORD Chicago O'Hare Intl
1h 23mnonstop
5:22 pm - 6:30 pmORD Chicago O'Hare Intl-CMI Champaign University-Willard
1h 08mnonstop
$271American Airlines
Useful Info
Good to know
Low season | February |
|---|---|
High season | November |
Cheapest flight | $49 |
FAQs for booking flights from Illinois to Chicago
Reviews of the top 3 airlines serving from Illinois to Chicago
7.6
ContourOverall score based on 44 reviews
6.2Entertainment
7.3Comfort
7.9Crew
6.9Food
7.6Boarding
Airline reviews
The crew was the friendly crew I’ve ever seen. After many many years. They were super friendly. They handed out candy for Halloween. They were just fantastic, which is so rare these days with flying not that other Cruz are not good. It’s just that these folks went above and beyond.
10.0 ExcellentAnonymous, Nov 2026
The crew was the friendly crew I’ve ever seen. After many many years. They were super friendly. They handed out candy for Halloween. They were just fantastic, which is so rare these days with flying not that other Cruz are not good. It’s just that these folks went above and beyond.
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.
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!
Fine except from Chicago to moline three different gate changes and flight times
When booking, the connection times seem fine. But in reality, my two connections were cut short by the first leg being delayed due to issues at the destination (too much traffic going into SFO, ORD) and it became extremely stressful.
Flight and crew were great. Need more legroom and do not allow seats to recline.
We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.
Just sat on the run way after we arrived early
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 now boarding notification was not updated in the app until I was actually on the plan. This si a massive fail considering my flight was delayed several times. These types of failures add stress that could be avoided since I no longer feel comfortable leaving the boarding area to get food or visit a lounge. Had I used the notification from the app, I would have missed my flight. The secondly, the process of connecting to wifi on aa flights is clunky and could be streamlined better. the copy and past process feels like MVP, and you are well beyond that stage.
Both flights were late leaving due to repairs/switching gates. The crew and pilots, however, were professional and courteous. Most importantly, we arrived at our destination safely. The seats were comforable. That size should be standard for all economy class. American could improve its boarding process. I am not sure why you need 9 groups for a small regional plane.
It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight
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.
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 $103
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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.