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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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
STL — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$112
(Southwest)

One-way from

$49
(Southwest)

Good round-trip deal

$128 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Kansas City Downtown-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Kansas City Downtown-Chicago (CHI) flights.
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From Missouri to Chicago (CHI)
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One-way flight from Missouri to Chicago (CHI)
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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 March 28, 2025.

This Southwest deal was found by Cheapflights users on 3/27. 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 4/266:00 amSTL - MDW
Nonstop1h 05mSouthwest
Mon 4/286:25 pmMDW - STL
Nonstop1h 10mSouthwest
Deal found 3/27$112
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/1912:00 pmSTL - ORD
Nonstop1h 24mAmerican Airlines
Tue 4/294:45 pmORD - STL
Nonstop1h 17mAmerican Airlines
Deal found 3/27$112
This Southwest deal was found by Cheapflights users on 3/26. 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 4/168:00 amSTL - ORD
1 stop6h 00mSouthwest
Wed 4/164:00 pmORD - STL
1 stop6h 10mSouthwest
Deal found 3/26$117
This Mytrip deal was found by Cheapflights users on 3/26. 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 4/258:40 amCGI - ORD
Nonstop1h 40mContour
Fri 5/25:00 pmORD - CGI
Nonstop1h 35mContour
Deal found 3/26$126
This Mytrip deal was found by Cheapflights users on 3/27. 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 4/2412:15 pmSTL - ORD
1 stop3h 35mSouthern / Mokulele
Mon 4/288:25 amORD - STL
1 stop11h 45mSouthern / Mokulele
Deal found 3/27$136
This Trip.com deal was found by Cheapflights users on 3/27. 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 4/1110:35 amUIN - ORD
Nonstop1h 57mSouthern / Mokulele
Tue 4/151:10 pmORD - UIN
Nonstop1h 55mSouthern / Mokulele
Deal found 3/27$152
This Delta deal was found by Cheapflights users on 3/27. 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.
Thu 4/241:46 pmSTL - MDW
1 stop4h 34mDelta
Mon 4/284:59 pmMDW - STL
1 stop6h 37mDelta
Deal found 3/27$177
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/46:38 pmSTL - MDW
1 stop10h 45mFrontier
Sat 4/512:58 pmMDW - STL
1 stop10h 48mFrontier
Deal found 3/27$179
This Delta deal was found by Cheapflights users on 3/27. 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 4/196:00 amSTL - ORD
2 stops6h 39mDelta
Tue 4/299:55 amORD - STL
1 stop6h 31mDelta
Deal found 3/27$182
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/116:38 pmSTL - ORD
1 stop10h 30mMultiple Airlines
Mon 4/148:25 amORD - STL
1 stop11h 45mMultiple Airlines
Deal found 3/27$183
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Tue 4/14:57 pmSTL - ORD
1 stop17h 43mFrontier
Tue 4/89:34 amORD - STL
1 stop14h 12mFrontier
Deal found 3/27$186
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/265:25 amSGF - ORD
Nonstop1h 40mAmerican Airlines
Sat 5/31:50 pmORD - SGF
Nonstop1h 44mAmerican Airlines
Deal found 3/27$189

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 March 28, 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 - ORD

STLORD

Lambert-St Louis

Sat 4/19

12:00 pm-1:24 pm

Nonstop1h 24m

Chicago O'Hare Intl

Tue 4/29

4:45 pm-6:02 pm

Nonstop1h 17m

$112

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 4/24

8:05 am-12:00 pm

1 stop3h 55m

Chicago Midway

Mon 4/28

5:45 am-10:45 am

1 stop5h 00m

$117

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Wed 4/16

8:00 am-2:00 pm

1 stop6h 00m

Chicago O'Hare Intl

Wed 4/16

4:00 pm-10:10 pm

1 stop6h 10m

$117

Cape GirardeauChicago

CGI - ORD

CGIORD

Cape Girardeau

Fri 4/25

8:40 am-10:20 am

Nonstop1h 40m

Chicago O'Hare Intl

Fri 5/2

5:00 pm-6:35 pm

Nonstop1h 35m

$126

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Thu 4/24

12:15 pm-3:50 pm

1 stop3h 35m

Chicago O'Hare Intl

Mon 4/28

8:25 am-8:10 pm

1 stop11h 45m

$136

QuincyChicago

UIN - ORD

UINORD

Quincy Regional

Fri 4/11

10:35 am-12:32 pm

Nonstop1h 57m

Chicago O'Hare Intl

Tue 4/15

1:10 pm-3:05 pm

Nonstop1h 55m

$152

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 4/24

1:46 pm-6:20 pm

1 stop4h 34m

Chicago Midway

Mon 4/28

6:45 pm-11:36 pm

1 stop4h 51m

$177

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 4/7

6:38 pm-5:23 am

1 stop10h 45m

Chicago Midway

Tue 4/8

4:40 pm-11:46 pm

1 stop7h 06m

$179

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Sat 4/19

6:00 am-12:39 pm

2 stops6h 39m

Chicago O'Hare Intl

Tue 4/29

9:55 am-4:26 pm

1 stop6h 31m

$182

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Fri 4/11

6:38 pm-5:08 am

1 stop10h 30m

Chicago O'Hare Intl

Mon 4/14

8:25 am-8:10 pm

1 stop11h 45m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 $323). 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 March 28, 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 March 28, 2025.

The most flights from USMO to CHI are scheduled on a Friday (65 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (10 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 March 28, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $49 on Southwest. Other airlines that offer cheap prices include United Airlines from $49 and Southern / Mokulele from $56 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 Lambert-St Louis - Chicago Midway as they are the most popular.

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

    Consider Iberia (93%), Copa Airlines (93%) or Royal Jordanian (91%) 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 $100. On average you can expect to pay $2,368. The most popular route, (Kansas City - Chicago O'Hare Intl), can usually be booked for $197.

  • 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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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Boston to Midway flights
Baltimore to Midway flights
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Reagan-National to Midway flights
George Bush Intcntl to O'Hare Intl flights
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Hobby to Midway flights

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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$86Average$154FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$115Average$308FlexibilityNo cancel feeOn-time71%
Southern / MokuleleCheapest$118Average$182FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$123Average$309FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$168Average$309FlexibilityNo cancel feeOn-time63%
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