$98 Find Cheap Flights from Chicago to Illinois - 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 from Chicago to Illinois departing on 8/17. 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

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Cheap Flights from Chicago to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
St. Louis
St. Louis1 stop$294
St. Louis
St. Louis1 stop$294

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

Sun, Aug 2 - Wed, Aug 5
Frontier Logo
6:05 am - 5:37 pm
MDW
-
STL
11h 32m
1 stop
Frontier Logo
4:57 pm - 10:03 pm
STL
-
MDW
5h 06m
1 stop
$294Frontier
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
9:55 am - 4:40 pm
MDW
-
STL
6h 45m
2 stops
Southwest Logo
7:50 am - 1:20 pm
STL
-
MDW
5h 30m
2 stops
$296Southwest
Tue, Aug 4 - Wed, Aug 5
Frontier Logo
12:11 pm - 5:37 pm
MDW
-
STL
5h 26m
1 stop
Frontier Logo
8:08 pm - 9:51 am
STL
-
MDW
13h 43m
2 stops
$299Frontier
Sun, Jul 19 - Mon, Jul 20
Frontier Logo
6:05 am - 5:37 pm
MDW
-
STL
11h 32m
1 stop
Frontier Logo
4:57 pm - 10:03 pm
STL
-
MDW
5h 06m
1 stop
$300Frontier
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
9:55 am - 4:40 pm
MDW
-
STL
6h 45m
2 stops
Southwest Logo
5:40 pm - 10:20 pm
STL
-
MDW
4h 40m
1 stop
$301Southwest
Thu, Jul 30 - Thu, Aug 6
Frontier Logo
9:27 pm - 8:57 am
MDW
-
STL
35h 30m
2 stops
Frontier Logo
6:34 pm - 9:51 am
STL
-
MDW
15h 17m
1 stop
$302Frontier
Thu, Aug 6 - Sun, Aug 9
Frontier Logo
11:06 am - 5:37 pm
MDW
-
STL
6h 31m
1 stop
Frontier Logo
6:34 pm - 5:22 pm
STL
-
MDW
22h 48m
2 stops
$304Frontier
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
11:50 am - 5:22 pm
MDW
-
STL
5h 32m
1 stop
Frontier Logo
6:17 pm - 10:55 am
STL
-
MDW
16h 38m
1 stop
$305Frontier
Wed, Jul 29 - Tue, Aug 4
Southwest Logo
3:15 pm - 8:20 pm
MDW
-
STL
5h 05m
1 stop
Southwest Logo
2:50 pm - 7:20 pm
STL
-
MDW
4h 30m
1 stop
$306Southwest
Fri, Aug 21 - Sun, Aug 23
Southwest Logo
5:50 pm - 7:05 pm
MDW
-
STL
1h 15mnonstop
Southwest Logo
12:55 pm - 2:05 pm
STL
-
MDW
1h 10mnonstop
$307Southwest
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.

How long does a flight from Chicago Midway Airport to Illinois take?

The duration of a flight to Illinois depends on your arrival airport. The shortest routes to Illinois from Chicago Midway Airport are to Peoria, which takes 23h 48m, and Bloomington, which takes 32h 18m.

Find deals

Good to know

Low seasonAugust
Cheapest flight$98
Best time to beat the crowds with an average 83% drop in price.
Most popular time to fly with an average 66% 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)