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 12/4. 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
$97
Overall average: $243
Southwest
Thu 12/4Mon 12/8
STL - MDW • Non-stop
Cheapest one-way
$49
Typical prices: $108-$155
Southwest
Thu 12/4
STL - MDW • Non-stop
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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, Dec 4 - Mon, Dec 8
Southwest Logo
7:35 pm - 8:45 pmSTL-MDW
1h 10mnonstop
Southwest Logo
6:20 am - 7:35 amMDW-STL
1h 15mnonstop
$97Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
2:25 pm - 7:20 pmSTL-MDW
4h 55m1 stop
Southwest Logo
6:20 am - 7:35 amMDW-STL
1h 15mnonstop
$107Southwest
Find Deal
Thu, Nov 27 - Thu, Dec 4
Southwest Logo
1:05 pm - 2:15 pmSTL-MDW
1h 10mnonstop
Southwest Logo
9:05 pm - 10:20 pmMDW-STL
1h 15mnonstop
$109Southwest
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Thu, Dec 4 - Mon, Dec 8
Frontier Logo
12:04 pm - 10:12 pmSTL-MDW
10h 08m1 stop
Frontier Logo
3:10 pm - 10:33 pmMDW-STL
7h 23m1 stop
$130Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
12:04 pm - 10:12 pmSTL-MDW
10h 08m1 stop
Frontier Logo
3:10 pm - 10:33 pmMDW-STL
7h 23m1 stop
$131Frontier
Find Deal
Tue, Feb 24 - Wed, Feb 25
Delta Logo
5:00 pm - 9:46 pmSTL-MDW
4h 46m1 stop
Delta Logo
5:25 pm - 11:40 pmMDW-STL
6h 15m1 stop
$157Delta
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Tue, Feb 24 - Wed, Feb 25
Delta Logo
7:30 am - 12:01 pmSTL-MDW
4h 31m1 stop
Delta Logo
2:00 pm - 11:40 pmMDW-STL
9h 40m2 stops
$162Delta
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Thu, Jan 8 - Sun, Jan 11
Multiple Airlines Logo
12:20 pm - 11:25 pmSTL-MDW
11h 05m2 stops
Multiple Airlines Logo
10:18 am - 10:33 pmMDW-STL
12h 15m1 stop
$205Multiple Airlines
Find Deal
Mon, Jan 5 - Thu, Jan 8
Allegiant Air Logo
7:03 pm - 11:53 amMLI-MDW
16h 50m1 stop
Allegiant Air Logo
10:17 am - 5:01 pmMDW-MLI
30h 44m1 stop
$325Allegiant Air
Find Deal
Wed, Nov 12 - Sun, Nov 16
Allegiant Air Logo
10:44 am - 3:43 pmPIA-MDW
28h 59m1 stop
Allegiant Air Logo
4:33 pm - 7:44 amMDW-PIA
15h 11m1 stop
$367Allegiant Air
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$49
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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)

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