STL - CHI

$59 Find Cheap Flights from St. Louis to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from St. Louis to Chicago departing on 5/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from St. Louis to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from St. Louis to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$171
Typical prices: $361-$247
Frontier
Sat 5/2Sat 5/9
STL - ORD • 1 stop
Cheapest non-stop
$186
Typical prices: $396-$248
Alaska Airlines
Thu 4/30Mon 5/4
STL - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Main Cabin Extra offers early boarding perks.
Use the CTA Orange Line from MDW for quick downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $171 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 1h 25m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 11% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $80 (round-trip)
Shortest trip • 3h 30m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 65% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 35% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from St. Louis to Chicago (STL-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from St. Louis to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from St. Louis to Chicago

Sat, May 2 - Sat, May 9
Frontier Logo
8:17 pm - 9:45 am
STL
-
ORD
13h 28m
1 stop
Frontier Logo
5:30 pm - 12:21 am
ORD
-
STL
6h 51m
1 stop
$171Frontier
Fri, Apr 17 - Tue, Apr 21
Frontier Logo
8:23 pm - 6:37 pm
STL
-
MDW
22h 14m
1 stop
Frontier Logo
2:15 pm - 6:50 am
MDW
-
STL
16h 35m
1 stop
$172Frontier
Thu, May 14 - Tue, May 19
Multiple Airlines Logo
6:55 pm - 11:59 pm
STL
-
ORD
29h 04m
2 stops
Multiple Airlines Logo
6:55 am - 8:55 am
ORD
-
STL
26h 00m
1 stop
$172Multiple Airlines
Wed, Apr 29 - Thu, Apr 30
Southwest Logo
8:30 am - 3:05 pm
STL
-
MDW
6h 35m
1 stop
Southwest Logo
8:20 am - 1:35 pm
MDW
-
STL
5h 15m
1 stop
$174Southwest
Wed, Apr 29 - Thu, Apr 30
Multiple Airlines Logo
8:23 pm - 10:23 am
STL
-
ORD
14h 00m
1 stop
Multiple Airlines Logo
4:28 pm - 6:50 am
ORD
-
STL
14h 22m
1 stop
$174Multiple Airlines
Wed, Apr 22 - Tue, Apr 28
Frontier Logo
8:23 pm - 9:17 pm
STL
-
ORD
24h 54m
2 stops
Frontier Logo
6:08 pm - 6:50 am
ORD
-
STL
12h 42m
1 stop
$175Frontier
Thu, Apr 30 - Mon, May 4
Multiple Airlines Logo
11:21 am - 10:23 am
STL
-
ORD
23h 02m
1 stop
Multiple Airlines Logo
7:33 pm - 8:55 am
ORD
-
STL
37h 22m
2 stops
$178Multiple Airlines
Mon, Apr 27 - Tue, Apr 28
Southwest Logo
10:30 am - 4:05 pm
STL
-
MDW
5h 35m
1 stop
Southwest Logo
11:35 am - 5:55 pm
MDW
-
STL
6h 20m
2 stops
$179Southwest
Thu, Apr 30 - Thu, May 7
Southwest Logo
1:45 pm - 2:55 pm
STL
-
MDW
1h 10mnonstop
Southwest Logo
9:30 pm - 10:45 pm
MDW
-
STL
1h 15mnonstop
$191Southwest
Tue, May 5 - Fri, May 8
Southwest Logo
5:35 am - 6:45 am
STL
-
MDW
1h 10mnonstop
Southwest Logo
11:40 am - 12:55 pm
MDW
-
STL
1h 15mnonstop
$197Southwest
Booking Insights

KAYAK's insights & trends for St. Louis to Chicago flights

Get data-powered insights and trends into flights from St. Louis to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from St. Louis to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from St. Louis to Chicago departing in May.

What is the cheapest St. Louis to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from St. Louis to Chicago costs $231 on the route between St. Louis (STL) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 11% cheaper than other St. Louis-Chicago routes. The most popular route is between St. Louis (STL) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from St. Louis to Chicago?

The average price of all round-trip flights from St. Louis to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from St. Louis to Chicago. For your return ticket, we recommend flying on a Saturday and avoiding Mondays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from St. Louis to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from St. Louis to Chicago is August, where tickets cost $205 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $505 and $448 respectively.

Can I save money by flying with a layover from St. Louis to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $224 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from St. Louis to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from St. Louis to Chicago, you should book around 4 weeks before departure, which saves you about 65% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Expert advice

Expert advice for your flight from St. Louis to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Qatar Airways, United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Jessica Macdonald

Jessica Macdonald

Expert on Lufthansa

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Duncan Madden

Duncan Madden

Expert on British Airways

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Yulia Denisyuk

Yulia Denisyuk

Expert on STL

Yulia is a freelance journalist who’s dispatched from 90+ countries. Her work focuses on cultures, adventure trips and air travel, appearing in NatGeo, NYT, CNTraveler, and more. For past assignments, she’s stayed with nomads in Mongolia and learned the art of Imigongo in Rwanda. She’s based in Chicago; in winter she often questions that decision.

Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds but there is an average 59% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from St. Louis to Chicago Midway Airport

When to book flights from St. Louis to Chicago

Are your dates flexible? Find out the best times to travel from St. Louis to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from St. Louis to Chicago

  • What is the cheapest flight from St. Louis to Chicago?

    In the last 3 days, the lowest price for a flight from St. Louis to Chicago was $59 for a one-way ticket and $171 for a round-trip.

  • Do I need a passport to fly between St. Louis and Chicago?

    A passport is not required to fly from St. Louis to Chicago.

  • Which airports will I be using when flying from St. Louis to Chicago?

    When flying out of St. Louis you will be using Lambert-St Louis. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from St. Louis to Chicago?

    American Airlines, Air Canada, Delta, and Lufthansa offer inflight Wi-Fi service on the St. Louis to Chicago flight route.

  • Which aircraft models fly most regularly from St. Louis to Chicago?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the St. Louis to Chicago flight route.

  • Which airline alliances offer flights from St. Louis to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between St. Louis and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from St. Louis to Chicago?

    There are nonstop flights from St. Louis to Chicago on a daily basis.

  • Which is the best airline for flights from St. Louis to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from St. Louis to Chicago are Southwest and United Airlines. With an average price for the route of $313 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $314 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from St. Louis to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from St. Louis to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from St. Louis to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from St. Louis is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from St. Louis to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to St. Louis with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from St. Louis to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from St. Louis up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from St. Louis to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $222 or less one-way and $384 or less round-trip.

Prefer to fly direct from St. Louis to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Lambert-St Louis to Chicago.
Find which airlines fly direct from Lambert-St Louis Airport to Chicago, which days they fly and book direct flights.

Direct departures

Lambert-St Louis to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Lambert-St Louis

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top 4 airlines serving from St. Louis to Chicago

 
See real verified KAYAK customer reviews for airlines flying from St. Louis to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from St. Louis to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4340 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

2.0 MediocreJames, Apr 2026
LAX - MCO
Read more Southwest reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

Both were great flights with wonderful pilots! It was not fancy, very simple. But boarding was super easy and the flight was smooth. Pick up in DFW was at corporate terminal which was the only confusing part for uber but if you call the uber driver and drop a pin they come right to it.

Totally great experience. Would definitely travel with them again. Thanks.

Both my fights got cancelled. Said mechanical issues but on flight tracker the flights came in and left! We were lied to!!

Was very impressed they called to confirm he would be on the flight. Great customer service!

We had a wonderful flight due to the care of our experienced pilot and copilot and the magnificent air views from our comfortable seats. What excitement to be in such a small plane with such magnificent around us.

Multiple time changes, then we left earlier than we were told.

Communication could be better but the staff and crew were over the top friendly and helpful, The flight itself was smooth.

flight was cancelled literally at 10pm the night before an early morning flight with hardly any time to reschedule. Will never book with kayak again.

My flight was cancelled 12 hours before takeoff. I was not able to reschedule another flight to make connections and had to cancel the entire trip. The ticket that was supposed to replace the cancelled flight had no boarding pass and I was unable to get one at the airport so I was denied access to the rescheduled flight. I was refunded but I missed my daughter's birthday.

I had a family emergency and couldn’t make the flight, and they wouldn’t let me cancel/refund it (a *month* ahead of time), were especially difficult with me on the phone, and wouldn’t let me even so much as reschedule the flight or get credit.

Everything you need to know for your flight from St. Louis to Chicago

Information on your arrival and departure airports

Compare transportation modes for St. Louis to Chicago

Transportation modeAverage priceAverage duration
Flights$7541h 10m
Trains$975h 10m
Buses$908h 05m