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$49+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
STL — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

September

Average price

$254

Good round-trip deal

$138 or less

Good one-way deal

$61 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. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/235:40 amSTL - MDW
Nonstop1h 10mSouthwest
Mon 10/277:40 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 9/15$97
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:28 pmSTL - ORD
Nonstop1h 25mUnited Airlines
Sat 10/189:25 amORD - STL
Nonstop1h 24mUnited Airlines
Deal found 9/13$97
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/237:16 amSTL - ORD
Nonstop1h 27mAmerican Airlines
Mon 10/2710:34 pmORD - STL
Nonstop1h 20mAmerican Airlines
Deal found 9/14$98
This American Airlines deal was found by Cheapflights users on 9/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:25 pmSTL - ORD
Nonstop1h 33mAmerican Airlines
Sat 10/116:53 pmORD - STL
Nonstop1h 33mAmerican Airlines
Deal found 9/12$99
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/285:40 amUIN - ORD
Nonstop1h 44mSouthern / Mokulele
Thu 10/25:10 pmORD - UIN
Nonstop1h 44mSouthern / Mokulele
Deal found 9/13$102
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Fri 11/215:30 pmUIN - ORD
Nonstop1h 20mContour
Sun 11/307:30 pmORD - UIN
Nonstop1h 20mContour
Deal found 9/14$106
This Southern / Mokulele deal was found by Cheapflights users on 9/15. 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 9/305:40 amUIN - ORD
Nonstop1h 44mSouthern / Mokulele
Sat 10/41:10 pmORD - UIN
Nonstop1h 44mSouthern / Mokulele
Deal found 9/15$108
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 11/197:00 amSTL - MDW
Nonstop1h 10mSouthwest
Mon 11/249:30 amMDW - STL
2 stops4h 45mSouthwest
Deal found 9/13$112
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:00 pmSTL - ORD
Nonstop1h 26mAmerican Airlines
Sun 11/96:44 amORD - STL
Nonstop1h 25mAmerican Airlines
Deal found 9/13$115
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 10/205:55 amSTL - ORD
1 stop6h 50mSouthwest
Tue 10/211:30 pmORD - STL
1 stop5h 35mSouthwest
Deal found 9/15$117
This Southwest deal was found by Cheapflights users on 9/13. 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.
Tue 10/141:30 pmSTL - ORD
1 stop9h 35mSouthwest
Wed 10/227:30 amORD - STL
1 stop7h 15mSouthwest
Deal found 9/13$122
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:25 pmSTL - ORD
Nonstop1h 25mUnited Airlines
Sun 10/199:25 amORD - STL
Nonstop1h 24mUnited Airlines
Deal found 9/12$133

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 September 15, 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 10/23

5:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

Mon 10/27

7:40 am-8:50 am

Nonstop1h 10m

$97

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Sat 11/8

7:58 pm-9:29 pm

Nonstop1h 31m

Chicago O'Hare Intl

Tue 11/11

3:23 pm-4:47 pm

Nonstop1h 24m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 11/19

7:00 am-8:10 am

Nonstop1h 10m

Chicago Midway

Mon 11/24

6:45 am-8:00 am

Nonstop1h 15m

$97

QuincyChicago

UIN - ORD

UINORD

Quincy Regional

Sun 9/28

5:40 am-7:24 am

Nonstop1h 44m

Chicago O'Hare Intl

Thu 10/2

5:10 pm-6:54 pm

Nonstop1h 44m

$102

QuincyChicago

UIN - ORD

UINORD

Quincy Regional

Fri 11/21

5:30 pm-6:50 pm

Nonstop1h 20m

Chicago O'Hare Intl

Sun 11/30

7:30 pm-8:50 pm

Nonstop1h 20m

$106

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 10/20

5:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

Mon 10/20

6:00 pm-9:30 pm

1 stop3h 30m

$107

QuincyChicago

UIN - ORD

UINORD

Quincy Regional

Tue 9/30

5:40 am-7:24 am

Nonstop1h 44m

Chicago O'Hare Intl

Sat 10/4

1:10 pm-2:54 pm

Nonstop1h 44m

$108

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Fri 11/14

6:43 pm-8:13 pm

Nonstop1h 30m

Chicago O'Hare Intl

Sat 11/15

2:20 pm-3:46 pm

Nonstop1h 26m

$115

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Sat 11/15

6:00 am-7:30 am

Nonstop1h 30m

Chicago O'Hare Intl

Sun 11/23

2:50 pm-4:16 pm

Nonstop1h 26m

$115

QuincyChicago

UIN - ORD

UINORD

Quincy Regional

Tue 3/10

9:50 am-11:10 am

Nonstop1h 20m

Chicago O'Hare Intl

Wed 3/11

7:30 pm-8:50 pm

Nonstop1h 20m

$118

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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 September 15, 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 September 15, 2025.

The most flights from USMO to CHI are scheduled on a Monday (78 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (55 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.

  • How long is the flight from Missouri to Chicago?

    Southwest, American Airlines, and Southern / Mokulele can get you from Missouri to Chicago in just under 1h 10m. Your travel time will be generally consistent. Missouri and Chicago are separated by a distance of 251 mi. Generally, flights for this route are nonstop.

  • 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 $49 on Southwest. Other airlines that offer cheap prices include United Airlines from $49 and Southern / Mokulele from $54 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 Kansas City - Chicago Midway as they are the most popular.

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

    Consider Qatar Airways (80%), Avianca (80%) or Japan Airlines (78%) 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 $99. On average you can expect to pay $916. The most popular route, (Kansas City - Chicago O'Hare Intl), can usually be booked for $133.

  • 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$117Average$307FlexibilityNo cancel feeOn-time71%
ContourCheapest$123Average$163FlexibilityNo cancel feeOn-timeN/A
Southern / MokuleleCheapest$140Average$217FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$143Average$335FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$151Average$317FlexibilityNo cancel feeOn-time63%

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