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$46+ Cheap flights from Missouri to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
STL — CHI
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap flight deals from Missouri to Chicago

Keep the following information in mind while searching for Missouri to Chicago flight deals. Data was last updated August 13, 2025.

Round-trip from

$87
(Southwest)

One-way from

$46
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$293

Good round-trip deal

$125 or less

Good one-way deal

$140 or less
From Missouri to Chicago (CHI)
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One-way flight from Missouri to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Missouri to Chicago (CHI).
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Price to beat on a one-way flight from Missouri to Chicago (CHI).
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Find flight deals from Missouri to Chicago

Cheapest flights from Missouri to Chicago
Explore the most affordable flight options available from Missouri to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:30 amSTL - MDW
1 stop7h 15mSouthwest
Mon 9/1511:45 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/12$87
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:10 amSTL - ORD
Nonstop1h 20mAmerican Airlines
Mon 9/1510:34 pmORD - STL
Nonstop1h 14mAmerican Airlines
Deal found 8/11$91
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/137:15 amSTL - MDW
2 stops6h 15mSouthwest
Tue 9/238:25 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 8/12$92
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:23 amSTL - ORD
Nonstop1h 22mAmerican Airlines
Mon 9/86:59 pmORD - STL
Nonstop1h 26mAmerican Airlines
Deal found 8/11$92
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:00 amSTL - MDW
1 stop4h 50mSouthwest
Mon 9/84:35 pmMDW - STL
1 stop4h 15mSouthwest
Deal found 8/13$97
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:10 amSTL - ORD
1 stop5h 35mSouthwest
Sat 9/62:55 pmORD - STL
1 stop5h 35mSouthwest
Deal found 8/12$97
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/131:45 pmSTL - ORD
2 stops8h 15mSouthwest
Tue 9/231:50 pmORD - STL
1 stop8h 05mSouthwest
Deal found 8/12$102
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:25 amSTL - ORD
1 stop6h 20mSouthwest
Thu 9/117:30 amORD - STL
2 stops11h 05mSouthwest
Deal found 8/12$108
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/411:50 amSTL - MDW
Nonstop1h 05mSouthwest
Sat 9/67:40 pmMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/12$114
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:10 amSTL - ORD
Nonstop1h 20mAmerican Airlines
Tue 9/1612:01 pmORD - STL
Nonstop1h 22mAmerican Airlines
Deal found 8/10$117
This Southern / Mokulele deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:40 amUIN - ORD
Nonstop1h 44mSouthern / Mokulele
Tue 9/161:10 pmORD - UIN
Nonstop1h 44mSouthern / Mokulele
Deal found 8/11$118
This Mytrip deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/209:10 amCGI - ORD
Nonstop1h 40mContour
Thu 9/255:30 pmORD - CGI
Nonstop1h 35mContour
Deal found 8/11$123

Cheapflights Fare Finder

 
Customize your flight search to find flights from Missouri to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 13, 2025.
Use the filters below to find and compare flights from Missouri to Chicago that are best for you.

Fly from

Missouri

Fly to

Chicago

Route

Depart

Return

Price

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 9/4

1:50 pm-6:05 pm

1 stop4h 15m

Chicago Midway

Mon 9/8

2:35 pm-3:45 pm

Nonstop1h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

11:55 am-6:35 pm

1 stop6h 40m

Chicago Midway

Tue 9/23

9:00 am-10:15 am

Nonstop1h 15m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

11:55 am-6:35 pm

1 stop6h 40m

Chicago Midway

Mon 9/15

11:45 am-12:55 pm

Nonstop1h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 9/4

7:50 am-12:40 pm

1 stop4h 50m

Chicago Midway

Sat 9/6

7:40 pm-8:50 pm

Nonstop1h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 9/2

8:15 am-12:50 pm

1 stop4h 35m

Chicago Midway

Tue 9/9

8:25 pm-9:40 pm

Nonstop1h 15m

$87

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Sat 11/8

6:00 am-7:30 am

Nonstop1h 30m

Chicago O'Hare Intl

Tue 11/11

3:23 pm-4:47 pm

Nonstop1h 24m

$91

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Mon 11/3

7:58 pm-9:29 pm

Nonstop1h 31m

Chicago O'Hare Intl

Sat 11/15

6:45 am-8:10 am

Nonstop1h 25m

$91

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Wed 9/17

7:23 am-8:45 am

Nonstop1h 22m

Chicago O'Hare Intl

Sat 9/20

7:10 pm-8:32 pm

Nonstop1h 22m

$91

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Sat 9/13

7:23 am-8:45 am

Nonstop1h 22m

Chicago O'Hare Intl

Tue 9/23

8:31 pm-9:53 pm

Nonstop1h 22m

$91

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Mon 9/22

7:23 am-8:45 am

Nonstop1h 22m

Chicago O'Hare Intl

Thu 9/25

8:00 am-9:26 am

Nonstop1h 26m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 60 results
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Best time to book a flight from Missouri to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Missouri with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Missouri to Chicago

What is the cheapest month to book a flight from Missouri to Chicago?

Currently, August is the cheapest month in which you can book a flight from Missouri to Chicago (average of $245). Flying from Missouri to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MO to CHI?

Find hourly flight availability from Missouri to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 13, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Missouri to Chicago as you normally would.

Weekly flight availability from Missouri to Chicago

Explore weekly flight availability from Missouri to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 13, 2025.

The most flights from USMO to CHI are scheduled on a Monday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 on average).

Related info for your journey

Find useful and relevant information for your journey from Missouri to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Missouri to Chicago one-way?

    One-way options have recently been found by users for as low as $46 on American Airlines. Other airlines that offer cheap prices include Southwest from $49 and Contour from $69 one-way.

  • What are the most popular routes from Missouri to Chicago?

    When deciding which route to take from Missouri to Chicago consider Kansas City - Chicago O'Hare Intl, Lambert-St Louis - Chicago O'Hare Intl or Springfield-Branson - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Missouri to Chicago?

    Consider Avianca (77%), Royal Jordanian (77%) or Qatar Airways (76%) when booking your flight. These represent the most reliable airlines when flying from Missouri to Chicago.

  • What are the cheapest flights from Missouri to Chicago?

    The cheapest flight price from Missouri to Chicago is $110. On average you can expect to pay $1,183. The most popular route, (Kansas City - Chicago O'Hare Intl), can usually be booked for $155.

  • Can I find deals for flights from Missouri to Chicago that include hotel bookings?

    Yes. In addition to deals on Missouri to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Missouri to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Missouri to Chicago.

  • Can I find deals for business class flights from Missouri to Chicago?

    Yes. Cheapflights offers flight deals from Missouri to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Missouri to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Missouri to Chicago (average of $245). Flying from Missouri to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Missouri to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Missouri to Chicago

Discover the top 5 airlines that operate flights from Missouri to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$106Average$162FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$115Average$308FlexibilityNo cancel feeOn-time71%
Southern / MokuleleCheapest$129Average$202FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$143Average$331FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$151Average$308FlexibilityNo cancel feeOn-time63%

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