MDW

$49 Find Cheap Flights from Illinois to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 2/15. 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 Chicago Midway Airport

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Everything you should know

Cheapest round-trip
$151
Overall average: $252
Frontier
Thu 1/8Fri 1/30
STL - MDW • 1 stop
Cheapest non-stop
$168
Typical prices: $97-$664
Southwest
Thu 11/27Thu 11/27
STL - MDW • Non-stop
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We hope you love your trip to Chicago!
Flight Deals
Useful Info
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, Jan 8 - Fri, Jan 30
Frontier Logo
3:43 pm - 10:17 pmSTL-MDW
6h 34m1 stop
Frontier Logo
6:20 am - 6:51 amMDW-STL
24h 31m1 stop
$151Frontier
Find Deal
Fri, Jan 30 - Sun, Feb 1
Frontier Logo
11:18 am - 7:52 pmSTL-MDW
8h 34m1 stop
Frontier Logo
5:01 pm - 6:51 amMDW-STL
13h 50m1 stop
$153Frontier
Find Deal
Thu, Nov 27 - Thu, Nov 27
Southwest Logo
6:25 am - 7:35 amSTL-MDW
1h 10mnonstop
Southwest Logo
9:30 am - 10:45 amMDW-STL
1h 15mnonstop
$168Southwest
Find Deal
Fri, Dec 12 - Sun, Dec 14
Frontier Logo
3:30 pm - 10:39 pmSTL-MDW
7h 09m1 stop
Frontier Logo
6:15 am - 9:52 amMDW-STL
27h 37m1 stop
$170Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
10:42 am - 1:59 pmSTL-MDW
27h 17m1 stop
Frontier Logo
6:37 pm - 8:59 amMDW-STL
14h 22m1 stop
$173Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
10:42 am - 1:59 pmSTL-MDW
27h 17m1 stop
Frontier Logo
6:37 pm - 8:59 amMDW-STL
14h 22m1 stop
$179Frontier
Find Deal
Thu, Jan 1 - Thu, Jan 8
Frontier Logo
10:42 am - 10:12 pmSTL-MDW
11h 30m1 stop
Frontier Logo
6:10 am - 2:48 pmMDW-STL
8h 38m1 stop
$190Frontier
Find Deal
Wed, Dec 31 - Thu, Jan 1
Delta Logo
5:50 am - 10:22 pmMLI-MDW
16h 32m1 stop
Delta Logo
6:00 am - 4:16 pmMDW-MLI
10h 16m1 stop
$585Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:59 pm - 9:08 amEVV-MDW
15h 09m2 stops
Delta Logo
6:17 pm - 10:30 amMDW-EVV
16h 13m2 stops
$620Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:59 pm - 9:08 amEVV-MDW
15h 09m2 stops
Delta Logo
1:49 pm - 10:30 amMDW-EVV
20h 41m2 stops
$672Delta
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from St. Louis to Chicago Midway Airport

FAQs for booking Illinois to Chicago flights

  • 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Chicago (MDW)