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Cheap Flights from Illinois to Chicago

 
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
Contour Logo
9:55 am - 11:40 amUIN  Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
Contour Logo
12:15 pm - 1:40 pmORD  Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$101Contour
Sun, Nov 8 - Thu, Nov 12
Contour Logo
9:55 am - 11:40 amUIN  Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
Contour Logo
12:15 pm - 1:40 pmORD  Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$101Contour
Mon, Nov 23 - Mon, Nov 30
Contour Logo
9:55 am - 11:40 amUIN  Quincy Regional-ORD Chicago O'Hare Intl
1h 45mnonstop
Contour Logo
12:15 pm - 1:40 pmORD  Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$102Contour
Sat, Nov 7 - Sun, Nov 8
United Airlines Logo
6:57 pm - 8:25 pmDEC  Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
United Airlines Logo
6:59 am - 8:09 amORD  Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Wed, Nov 4 - Sun, Nov 8
United Airlines Logo
6:57 pm - 8:25 pmDEC  Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
United Airlines Logo
6:59 am - 8:09 amORD  Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Tue, Nov 24 - Fri, Nov 27
United Airlines Logo
6:57 pm - 8:25 pmDEC  Decatur Arpt-ORD Chicago O'Hare Intl
1h 28mnonstop
United Airlines Logo
5:00 pm - 6:10 pmORD  Chicago O'Hare Intl-DEC Decatur Arpt
1h 10mnonstop
$149United Airlines
Mon, Nov 9 - Fri, Nov 13
Multiple Airlines Logo
2:40 pm - 11:13 pmUIN  Quincy Regional-ORD Chicago O'Hare Intl
32h 33m2 stops Nashville Intl Dallas/Fort Worth
Multiple Airlines Logo
12:15 pm - 1:40 pmORD  Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$251Multiple Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
10:21 am - 12:14 pmMWA  Marion Williamson County-ORD Chicago O'Hare Intl
1h 53mnonstop
American Airlines Logo
11:00 pm - 12:36 amORD  Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
10:21 am - 12:14 pmMWA  Marion Williamson County-ORD Chicago O'Hare Intl
1h 53mnonstop
American Airlines Logo
8:15 am - 9:51 amORD  Chicago O'Hare Intl-MWA Marion Williamson County
1h 36mnonstop
$261American Airlines
Mon, Nov 23 - Mon, Nov 30
Multiple Airlines Logo
2:40 pm - 7:47 amUIN  Quincy Regional-ORD Chicago O'Hare Intl
17h 07m2 stops Nashville Intl Dallas/Fort Worth
Multiple Airlines Logo
12:15 pm - 1:40 pmORD  Chicago O'Hare Intl-UIN Quincy Regional
1h 25mnonstop
$262Multiple Airlines
Useful Info

Good to know

Low season

February

Cheapest flight

$50
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly and prices are also 36% lower on average.
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.
7.5
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
Read more Contour 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..........

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.

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