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$59+ Cheap flights from St. Louis (STL) 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
STL — CHI
Jul 29 — Aug 51
Wed 7/29
Wed 8/5
1 adult, Economy
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Cheapflights Tip: The best prices from Lambert-St Louis to Chicago are usually found in August or September, booked 90 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap flight deals from St. Louis to Chicago

Cheapest flights from St. Louis to Chicago
Explore the most affordable flight options available from St. Louis to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 29, 2026.

This Southwest deal was found by Cheapflights users on 6/24. 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 9/175:40 pm
STL
-
MDW
1 stop4h 40m
Southwest
Mon 9/216:20 am
MDW
-
STL
1 stop3h 10m
Southwest
Deal found 6/24$215
This Delta deal was found by Cheapflights users on 6/24. 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.
Mon 9/141:55 pm
STL
-
ORD
1 stop6h 35m
Delta
Thu 9/241:55 pm
ORD
-
STL
1 stop6h 40m
Delta
Deal found 6/24$215
This Delta deal was found by Cheapflights users on 6/24. 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.
Mon 9/141:55 pm
STL
-
MDW
1 stop4h 38m
Delta
Sat 9/199:29 am
MDW
-
STL
1 stop5h 45m
Delta
Deal found 6/24$218
This Delta deal was found by Cheapflights users on 6/24. 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 7/2510:19 am
STL
-
ORD
1 stop6h 04m
Delta
Sat 8/111:10 am
ORD
-
STL
1 stop6h 09m
Delta
Deal found 6/24$218
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:35 am
STL
-
ORD
1 stop9h 09m
Frontier
Wed 9/232:03 pm
ORD
-
STL
1 stop19h 37m
Frontier
Deal found 6/24$220
This American Airlines deal was found by Cheapflights users on 6/25. 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 8/85:00 am
STL
-
ORD
Nonstop1h 24m
American Airlines
Mon 8/1011:00 pm
ORD
-
STL
Nonstop1h 14m
American Airlines
Deal found 6/25$225
This Southwest deal was found by Cheapflights users on 6/25. 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 10/55:40 am
STL
-
MDW
Nonstop1h 10m
Southwest
Wed 10/77:45 am
MDW
-
STL
Nonstop1h 15m
Southwest
Deal found 6/25$226
This United Airlines deal was found by Cheapflights users on 6/24. 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.
Mon 9/145:30 pm
STL
-
ORD
Nonstop1h 31m
United Airlines
Tue 9/228:30 pm
ORD
-
STL
Nonstop1h 30m
United Airlines
Deal found 6/24$226
This Southwest deal was found by Cheapflights users on 6/26. 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.
Sat 7/254:00 pm
STL
-
MDW
Nonstop1h 05m
Southwest
Fri 7/312:45 pm
MDW
-
STL
Nonstop1h 10m
Southwest
Deal found 6/26$227
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Sun 8/234:54 pm
STL
-
ORD
Nonstop1h 39m
American Airlines
Tue 8/2511:29 am
ORD
-
STL
Nonstop1h 25m
American Airlines
Deal found 6/24$227
This Frontier deal was found by Cheapflights users on 6/28. 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.
Tue 7/217:03 pm
STL
-
ORD
1 stop10h 34m
Frontier
Tue 7/287:05 am
ORD
-
STL
1 stop10h 32m
Frontier
Deal found 6/28$230
This Frontier deal was found by Cheapflights users on 6/29. 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.
Tue 10/275:32 pm
STL
-
ORD
1 stop12h 03m
Frontier
Sat 11/77:00 am
ORD
-
STL
1 stop15h 39m
Frontier
Deal found 6/29$233

Find flight deals from St. Louis to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from St. Louis (STL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$215
(Southwest)

One-way from

$59
(Southwest)

Popular in

January

Cheapest in

August

Average price

$344

Good round-trip deal

$346 or less

Good one-way deal

$216 or less
Provider with most accurate pricing for Lambert-St Louis-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Lambert-St Louis-Chicago (CHI) flights.
Search Deals
From Lambert-St Louis to Chicago (CHI)
Search Deals
One-way flight from Lambert-St Louis to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Lambert-St Louis to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Lambert-St Louis to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from St. Louis 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 29, 2026.
Use the filters below to find and compare flights from St. Louis to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Mon 9/14

1:55 pm-8:30 pm

1 stop6h 35m

Chicago O'Hare Intl

Thu 9/24

1:55 pm-8:35 pm

1 stop6h 40m

$215

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 9/17

6:40 am-12:39 pm

1 stop5h 59m

Chicago Midway

Tue 9/22

9:29 am-1:06 pm

1 stop3h 37m

$218

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Mon 9/14

5:30 pm-7:01 pm

Nonstop1h 31m

Chicago O'Hare Intl

Tue 9/22

8:30 pm-10:00 pm

Nonstop1h 30m

$226
Quickest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 7/25

4:00 pm-5:05 pm

Nonstop1h 05m

Chicago Midway

Fri 7/31

2:45 pm-3:55 pm

Nonstop1h 10m

$227

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 7/20

5:40 am-6:45 am

Nonstop1h 05m

Chicago Midway

Wed 7/22

10:00 am-11:15 am

Nonstop1h 15m

$238

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/8

6:45 am-1:05 pm

2 stops6h 20m

Chicago Midway

Mon 8/10

5:30 pm-10:05 pm

1 stop4h 35m

$243

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 8/8

6:45 am-1:05 pm

2 stops6h 20m

Chicago Midway

Wed 8/12

12:35 pm-4:45 pm

1 stop4h 10m

$252

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Thu 8/20

7:25 am-9:01 am

Nonstop1h 36m

Chicago O'Hare Intl

Sun 8/23

1:30 pm-2:57 pm

Nonstop1h 27m

$257

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sun 9/27

6:40 am-12:39 pm

1 stop5h 59m

Chicago Midway

Sat 10/3

9:29 am-3:14 pm

1 stop5h 45m

$257

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

Sun 9/27

6:40 am-10:37 am

1 stop3h 57m

Chicago O'Hare Intl

Sat 10/3

11:17 am-3:14 pm

1 stop3h 57m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/24

Showing 1-10 of 39 resultsSorted by cheapest first
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Compare providers for flights from St. Louis to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from St. Louis to Chicago in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on St. Louis-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on St. Louis-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from St. Louis-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on St. Louis-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for St. Louis-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from St. Louis to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Louis 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 St. Louis to Chicago

What is the cheapest month to book a flight from St. Louis to Chicago?

Currently, August is the cheapest month in which you can book a flight from St. Louis to Chicago (average of $61). Flying from St. Louis to Chicago in February is currently the most expensive (average of $117). 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 STL to CHI?

Find hourly flight availability from St. Louis 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 29, 2026.

It’s optimal to fly from St. Louis to Chicago in the morning. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from St. Louis to Chicago

Explore weekly flight availability from St. Louis 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 29, 2026.

The most flights from STL to CHI are scheduled on a Sunday (81 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (32 on average).

How much does it cost to fly round-trip from St. Louis to Chicago?

How far ahead should I book a flight from St. Louis to Chicago?

The price you pay for your flight from St. Louis to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 73 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from St. Louis to Chicago?

Use this chart to determine the cheapest time to fly round-trip from St. Louis to Chicago. Price data was last updated on June 27, 2026.

Travelers seeking maximum savings on their St. Louis to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for St. Louis to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your St. Louis to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Taryn White

Taryn White

Expert on STL

Taryn White is a freelance travel writer, digital creator, and travel advisor who has visited nearly 100 countries and all 50 states. She’s familiar with many airports and enjoys beach hopping, boutique hotels, spa experiences, and exploring local culture. Her work has appeared in Travel + Leisure, Condé Nast Traveler, National Geographic, Smithsonian Magazine, AFAR, and more.

Read more

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 29, 2026.
Read through reviews of airlines operating flights from St. Louis to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,246 reviews

Boarding

8.1

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,246 reviews
Southwest
7.9
Good
4,246 reviews

Boarding

8.1

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,895 reviews
Southwest
7.9
Good
4,246 reviews

Boarding

8.1

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,766 reviews
Southwest
7.9
Good
4,246 reviews

Boarding

8.1

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

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

  • What airport do you fly from for flights from St. Louis to Chicago?

    If you book a flight to Chicago from St. Louis, you will be flying from Lambert-St Louis, which is the city’s only airport. Lambert-St Louis (STL) is located 12.7 mi from the center of St. Louis. There are 61 flights from Lambert-St Louis to Chicago per day from 3 different airlines.

  • How long is the flight from St. Louis to Chicago?

    Departing from St. Louis to Chicago will take you 1h 05m. The distance between St. Louis and Chicago is about 251 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from St. Louis to Chicago round-trip?

    Cheapflights users have booked flights from St. Louis to Chicago round-trip from $97. Other airlines that can offer you cheap pricing are Southwest, from $137, and United Airlines, from $145. These flights start at 71% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from St. Louis to Chicago one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $48. American Airlines flights start at $57 while deals on United Airlines start at $75 one-way.

  • What are the most reliable airlines from St. Louis to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from St. Louis to Chicago on time: Republic Airways (82%), Turkish Airlines (82%), Alaska Airlines (78%).

  • What are the cheapest flights from St. Louis to Chicago?

    The cheapest flight price from St. Louis to Chicago is $168. On average you can expect to pay $1,406. The most popular route, (Lambert-St Louis - Chicago O'Hare Intl), can usually be booked for $117.

  • Can I find deals for flights from St. Louis to Chicago that include hotel bookings?

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

  • How can I find direct flights from St. Louis to Chicago?

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

  • Can I find deals for business class flights from St. Louis to Chicago?

    Yes. Cheapflights offers flight deals from St. Louis 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 St. Louis to Chicago?

    Currently, August is the cheapest month in which you can book a flight from St. Louis to Chicago (average of $61). Flying from St. Louis to Chicago in February is currently the most expensive (average of $117). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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Top 3 airlines flying from St. Louis to Chicago

Discover the top 3 airlines that operate flights from St. Louis 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$313FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$128Average$391FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$137Average$489FlexibilityNo cancel feeOn-time63%

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