$49 Find Cheap Flights from Chicago to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Illinois departing on 12/25. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Illinois, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Flight Deals

Cheap Flights from Chicago to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Bloomington
Bloomington2 stops$426
St. Louis
St. Louis1 stop$129
Bloomington
Bloomington2 stops$426
St. Louis
St. Louis1 stop$129

Book Cheap Chicago to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Illinois 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 Chicago to Illinois

Thu, Jan 8 - Sun, Jan 11
Frontier Logo
9:07 pm - 10:02 amMDW-STL
12h 55m1 stop
Frontier Logo
5:11 pm - 9:13 amSTL-MDW
16h 02m1 stop
$129Frontier
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Thu, Jan 1 - Mon, Jan 5
Southwest Logo
8:25 am - 9:40 amMDW-STL
1h 15mnonstop
Southwest Logo
5:45 pm - 6:55 pmSTL-MDW
1h 10mnonstop
$134Southwest
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Thu, Jan 1 - Mon, Jan 5
Southwest Logo
5:00 am - 10:10 amMDW-STL
5h 10m1 stop
Southwest Logo
5:45 pm - 6:55 pmSTL-MDW
1h 10mnonstop
$144Southwest
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Mon, Dec 8 - Wed, Dec 10
Southwest Logo
1:10 pm - 5:25 pmMDW-STL
4h 15m1 stop
Southwest Logo
7:00 am - 8:10 amSTL-MDW
1h 10mnonstop
$154Southwest
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Tue, Dec 16 - Wed, Dec 31
Delta Logo
6:00 am - 10:45 amMDW-STL
4h 45m1 stop
Delta Logo
5:13 pm - 10:22 pmSTL-MDW
5h 09m1 stop
$157Delta
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Mon, Feb 23 - Tue, Feb 24
Southwest Logo
8:15 am - 9:35 amMDW-STL
1h 20mnonstop
Southwest Logo
6:50 am - 1:55 pmSTL-MDW
7h 05m2 stops
$159Southwest
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Thu, Dec 4 - Sun, Dec 14
Frontier Logo
7:23 pm - 9:47 amMDW-STL
14h 24m1 stop
Frontier Logo
10:42 am - 6:12 pmSTL-MDW
7h 30m1 stop
$163Frontier
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Mon, Dec 8 - Wed, Dec 10
Southwest Logo
10:05 am - 4:05 pmMDW-STL
6h 00m1 stop
Southwest Logo
12:00 pm - 5:10 pmSTL-MDW
5h 10m1 stop
$164Southwest
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Mon, Feb 23 - Tue, Feb 24
Southwest Logo
1:25 pm - 7:30 pmMDW-STL
6h 05m1 stop
Southwest Logo
6:50 am - 1:55 pmSTL-MDW
7h 05m2 stops
$169Southwest
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Wed, Apr 15 - Sat, Apr 18
Delta Logo
10:35 am - 10:23 pmMDW-BMI
11h 48m1 stop
Delta Logo
6:01 am - 9:45 pmBMI-MDW
15h 44m1 stop
$639Delta
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Booking Insights

KAYAK's insights & trends for Chicago to Illinois flights

Get data-powered insights and trends into flights from Chicago to Illinois to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Chicago Midway Airport to Illinois?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Illinois were found on Frontier ($129) and Southwest ($134).

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Good to know

Low seasonOctober
Cheapest flight$49
Best time to beat the crowds with an average 69% drop in price.
Most popular time to fly with an average 92% increase in price.
Flight from Chicago Midway Airport to St. Louis

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Chicago to Illinois?

    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 Chicago to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to 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 Chicago to Illinois?

    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 from Chicago to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Illinois?

    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 from Chicago to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Chicago to Illinois

Information on your arrival and departure airports

Chicago (MDW)