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$59+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
STL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$97
(Southwest)

One-way from

$59
(Southwest)

Popular in

March

Cheapest in

September

Average price

$324

Good round-trip deal

$138 or less

Good one-way deal

$84 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/611:35 amSTL - MDW
Nonstop1h 05mSouthwest
Mon 8/186:05 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 6/11$97
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/218:50 amSTL - ORD
Nonstop1h 31mAmerican Airlines
Thu 9/410:34 pmORD - STL
Nonstop1h 14mAmerican Airlines
Deal found 6/11$97
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/95:40 amUIN - ORD
Nonstop1h 57mSouthern / Mokulele
Wed 7/161:10 pmORD - UIN
Nonstop1h 55mSouthern / Mokulele
Deal found 6/11$111
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/56:25 amSTL - ORD
1 stop6h 20mSouthwest
Wed 8/61:50 pmORD - STL
1 stop8h 05mSouthwest
Deal found 6/10$117
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/103:45 pmCGI - ORD
Nonstop1h 40mContour
Mon 8/1811:25 amORD - CGI
Nonstop1h 35mContour
Deal found 6/10$121
This Trip.com deal was found by Cheapflights users on 6/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:00 amSTL - ORD
Nonstop1h 30mUnited Airlines
Mon 8/119:20 pmORD - STL
Nonstop1h 25mUnited Airlines
Deal found 6/12$155
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/251:00 pmSTL - ORD
1 stop3h 32mSouthern / Mokulele
Sun 7/278:15 amORD - STL
1 stop3h 55mSouthern / Mokulele
Deal found 6/10$166
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/235:25 pmMCI - ORD
1 stop4h 35mSouthwest
Mon 8/255:45 pmORD - MCI
1 stop5h 00mSouthwest
Deal found 6/10$174
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:10 pmMCI - MDW
1 stop4h 40mSouthwest
Sat 8/168:00 amMDW - MCI
1 stop7h 40mSouthwest
Deal found 6/11$174
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/106:35 amMCI - ORD
1 stop6h 10mDelta
Tue 9/169:30 amORD - MCI
1 stop5h 29mDelta
Deal found 6/10$177
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/52:07 pmMCI - MDW
1 stop4h 33mDelta
Wed 8/139:31 amMDW - MCI
1 stop3h 47mDelta
Deal found 6/11$177
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:30 amSTL - MDW
1 stop6h 39mDelta
Tue 11/116:00 amMDW - STL
1 stop4h 40mDelta
Deal found 6/10$177

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 June 12, 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 8/7

6:00 pm-11:50 pm

1 stop5h 50m

Chicago Midway

Mon 8/11

7:30 am-8:40 am

Nonstop1h 10m

$87

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Thu 8/21

8:50 am-10:21 am

Nonstop1h 31m

Chicago O'Hare Intl

Thu 9/4

10:34 pm-11:48 pm

Nonstop1h 14m

$97

QuincyChicago

UIN - ORD

UINORD

Quincy Regional

Wed 7/9

5:40 am-7:37 am

Nonstop1h 57m

Chicago O'Hare Intl

Wed 7/16

1:10 pm-3:05 pm

Nonstop1h 55m

$111

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Tue 8/5

6:25 am-12:45 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 8/6

1:50 pm-9:55 pm

1 stop8h 05m

$117

Cape GirardeauChicago

CGI - ORD

CGIORD

Cape Girardeau

Thu 7/10

3:45 pm-5:25 pm

Nonstop1h 40m

Chicago O'Hare Intl

Mon 8/18

11:25 am-1:00 pm

Nonstop1h 35m

$121

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Thu 8/7

5:00 am-6:30 am

Nonstop1h 30m

Chicago O'Hare Intl

Mon 8/11

9:20 pm-10:45 pm

Nonstop1h 25m

$155

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Fri 7/25

1:00 pm-4:32 pm

1 stop3h 32m

Chicago O'Hare Intl

Sun 7/27

8:15 am-12:10 pm

1 stop3h 55m

$166

Kansas CityChicago

MCI - ORD

MCIORD

Kansas City

Sat 8/23

5:25 pm-10:00 pm

1 stop4h 35m

Chicago O'Hare Intl

Mon 8/25

5:45 pm-10:45 pm

1 stop5h 00m

$174

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Thu 8/14

7:10 pm-11:50 pm

1 stop4h 40m

Chicago Midway

Sat 8/16

8:00 am-3:40 pm

1 stop7h 40m

$174

Kansas CityChicago

MCI - ORD

MCIORD

Kansas City

Wed 9/10

6:35 am-12:45 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 9/16

9:30 am-2:59 pm

1 stop5h 29m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 12, 2025.

The most flights from USMO to CHI are scheduled on a Thursday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Missouri to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
725 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $59 on Southwest. Other airlines that offer cheap prices include Contour from $62 and United Airlines from $62 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 SkyWest Airlines (90%), Finnair (89%) or Copa Airlines (89%) 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 $120. On average you can expect to pay $2,443. The most popular route, (Kansas City - Chicago O'Hare Intl), can usually be booked for $109.

  • 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 Missouri?

Book flights to Missouri if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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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LaGuardia to Midway flights
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Los Angeles to Midway flights
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Boston to Midway flights
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Baltimore to Midway flights
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$86Average$158FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$115Average$305FlexibilityNo cancel feeOn-time71%
Southern / MokuleleCheapest$118Average$182FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$126Average$323FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$168Average$305FlexibilityNo cancel feeOn-time63%

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