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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$32 CHEAP FLIGHTS from Illinois to Chicago Midway (MDW)

MDW

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$71

Overall average: $252

Southwest

Sat 1/17Tue 1/20

STL - MDW • Non-stop

Cheapest one-way

$32

Typical prices: $253-$268

Southwest

Tue 1/20

STL - MDW • Non-stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

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.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Illinois to Chicago

Sat, Jan 17 - Tue, Jan 20

7:40 am - 8:50 amSTL-MDW

1h 10mnonstop

1:50 pm - 3:00 pmMDW-STL

1h 10mnonstop

$71Southwest

Find Deal

Sat, Jan 17 - Sun, Jan 18

5:50 pm - 7:00 pmSTL-MDW

1h 10mnonstop

9:55 am - 11:15 amMDW-STL

1h 20mnonstop

$88Southwest

Find Deal

Sat, Jan 17 - Sun, Jan 18

5:50 pm - 7:00 pmSTL-MDW

1h 10mnonstop

6:10 am - 7:35 amMDW-STL

1h 25mnonstop

$97Southwest

Find Deal

Sat, Jan 17 - Tue, Jan 20

7:40 am - 8:50 amSTL-MDW

1h 10mnonstop

1:25 pm - 6:55 pmMDW-STL

5h 30m1 stop

$121Southwest

Find Deal

Fri, Jan 16 - Fri, Jan 23

8:32 pm - 7:27 amSTL-MDW

10h 55m1 stop

1:00 pm - 11:33 pmMDW-STL

10h 33m1 stop

$143Frontier

Find Deal

Wed, Jan 14 - Wed, Jan 21

8:32 pm - 8:03 amSTL-MDW

11h 31m1 stop

1:20 pm - 11:33 pmMDW-STL

34h 13m2 stops

$149Frontier

Find Deal

Sat, Jan 17 - Sun, Jan 18

11:23 am - 4:16 pmSTL-MDW

4h 53m1 stop

7:16 pm - 11:25 pmMDW-STL

4h 09m1 stop

$157Delta

Find Deal

Sat, Jan 17 - Sun, Jan 18

11:23 am - 4:16 pmSTL-MDW

4h 53m1 stop

7:16 pm - 11:25 pmMDW-STL

4h 09m1 stop

$158Delta

Find Deal

Fri, Dec 19 - Sun, Dec 21

12:22 pm - 9:58 pmEVV-MDW

9h 36m1 stop

2:16 pm - 11:42 amMDW-EVV

21h 26m1 stop

$444Multiple Airlines

Find Deal

Fri, Dec 19 - Sun, Dec 21

12:22 pm - 10:12 pmEVV-MDW

9h 50m2 stops

2:16 pm - 11:42 amMDW-EVV

21h 26m1 stop

$493Multiple Airlines

Find Deal

Useful Info

Low season	February
High season	July
Cheapest flight	$32

Best time to beat the crowds with an average 12% drop in price.

Most popular time to fly with an average 2% increase in price.

Flight from St. Louis to Chicago Midway Airport

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.

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

Airports

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Information on your arrival and departure airports

Chicago (MDW)

MDW

$32 Find Cheap Flights from Illinois to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

Everything you should know

Cheap Flights from Illinois to Chicago

Recent round-trip flight deals from Illinois to Chicago

Recent one-way flight deals from Illinois to Chicago

Recent last minute flight deals from Illinois to Chicago

Recent direct flight deals from Illinois to Chicago

Good to know

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?

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Cabin class types available on flights to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Illinois

Choose which airport to fly into in Chicago

Find deals for your return flight