Can I fly direct from St. Louis to Chicago?

Yes, direct flights from St. Louis to Chicago are available. Historically, approximately 46% of the flights on this route have been direct. For journeys that include stopovers, travelers typically experience a median of 2 stopovers. This indicates a good chance of finding a non-stop option for your trip.

What's the flight time from St. Louis to Chicago?

The direct flight time from St. Louis to Chicago is typically 1 hour and 31 minutes, covering a distance of 404 kilometers. For flights with one stop, the median travel time is considerably longer, averaging 16 hours and 36 minutes. This difference highlights the convenience and efficiency of choosing a direct route when available.

How often do St. Louis to Chicago flight prices drop?

Historically, flight prices for the St. Louis to Chicago route have shown frequent drops across the trailing quarter. This suggests that travelers have regular opportunities to find more affordable fares. The frequent classification indicates that price fluctuations are common, making it beneficial to monitor prices for potential savings.

Flights From St. Louis

To Chicago

Cheap Flights from St. Louis to Chicago

Browse current best options from St. Louis. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

St. Louis

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

Prices updated 2 days ago

451 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 17, 2026.)

Today’s best flight deals from St. Louis to Chicago

Explore current cheapest deals departing from St. Louis to Chicago

2026-09-05 – 2026-09-06
STL - Chicago
71% AI deal score
$179
$117
Round trip
2026-09-24 – 2026-09-28
STL - Chicago
47% AI deal score
$143
$117
Round trip
2026-09-05 – 2026-09-08
STL - Chicago
71% AI deal score
$179
$117
Round trip
2026-09-14 – 2026-09-15
STL - Chicago
66% AI deal score
$175
$117
Round trip
2026-09-10 – 2026-09-14
STL - Chicago
67% AI deal score
$176
$117
Round trip
2026-09-10 – 2026-09-24
STL - Chicago
49% AI deal score
$144
$117
Round trip
2026-09-16 – 2026-09-23
STL - Chicago
66% AI deal score
$166
$117
Round trip
2026-09-17 – 2026-09-24
STL - Chicago
46% AI deal score
$138
$117
Round trip
2026-09-24 – 2026-09-26
STL - Chicago
66% AI deal score
$174
$117
Round trip
2026-09-16 – 2026-09-22
STL - Chicago
46% AI deal score
$138
$117
Round trip

St. Louis to Chicago: Overview

Insights for flights from St. Louis to Chicago

When considering cheap flights from St. Louis to Chicago, you'll find that February stands out as the most affordable month, with a median fare of just $169. January offers a similar value, also with a median fare of $169, making the early part of the year particularly economical for this route. Looking further into the spring, May presents another good option with a median fare of $249.

Fares for flights from St. Louis to Chicago typically range from $220–$760, with a median price of $407. Right now, current fares are significantly above the typical level for this route. Only 2% of recent fares were classified as a good price, indicating that finding deals might require some flexibility or advance planning. New deals appear almost daily, so setting up a price alert could be beneficial.

For direct flights from St. Louis to Chicago, a meaningful share of itineraries are non-stop, accounting for 46% of recent fares. For the remaining itineraries that include connections, the typical number of stopovers is 2. This means you have a reasonable chance of finding a non-stop option, but connecting flights are also common.

A typical journey from St. Louis to Chicago takes about 1h 31m, including any connections. This median duration reflects the overall travel time you can expect for this route. Given that a significant portion of flights include connections, this figure provides a realistic expectation for your total travel time.

The distance between St. Louis and Chicago is approximately 404 kilometers. This classifies the route as a short-haul flight, meaning you can expect a relatively quick journey between these two cities.

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

Regular price: $126 - $242

Prices for flights from St. Louis to Chicago are currently below the regular range.

The regular price range for flights from St. Louis to Chicago is between $126 and $242. The current lowest deal is $117 on Kayak for travel from Sep 5-Sep 7.

now $117

Low $126

High $242

The cheapest time to fly from St. Louis to Chicago

Flights from St. Louis to Chicago are cheapest in January, with a median price of $169. The most expensive month to fly is December, with a median price of $782. Prices are generally lower from January to September.

January

Cheapest

Flights from $169

December

Most Expensive

Flights from $782

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from St. Louis to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from St. Louis to Chicago

Mon, Aug 17

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (MDW)

Frontier Airlines

$549

$360

One-way

Fri, Aug 21

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (ORD)

Frontier Airlines

$466

$350

One-way

Fri, Aug 21

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (ORD)

Frontier Airlines

$477

$387

One-way

Wed, Sep 2

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (RFD)

Southern Airways

$300

$258

One-way

Fri, Sep 4

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (ORD)

$324

$144

One-way

Fri, Sep 4

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (ORD)

$325

$144

One-way

Biggest price drops on these dates for flights from St. Louis to Chicago

2 nights

Sep 4 - Sep 6

$325 → $144

56%

1 night

Sep 4 - Sep 5

$324 → $144

56%

3 nights

Sep 21 - Sep 24

$309 → $135

56%

3 nights

Sep 11 - Sep 14

$289 → $130

55%

Popular Airports to fly from St. Louis to Chicago

St. Louis - Chicago route insights

💸 Price insights

Recent fares below the typical level

Recent fares from St. Louis to Chicago are $117, which is below the typical level.

📅 Best time to fly

February and January are historically cheapest

Historically, February and January are the cheapest months to fly from St. Louis to Chicago.

⏱️ Flight duration

Direct flights average 1h 31m

Direct flights from St. Louis to Chicago typically take 1 hour and 31 minutes.

✈️ Airlines & availability

Mixed availability of direct flights

About 46% of recent flights from St. Louis to Chicago are direct, with mixed availability.

🏆 Airline highlight

American Airlines and Southwest offer direct flights

American Airlines and Southwest Airlines offer direct flights on this route.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from St. Louis to Chicago are frequently available.

St. Louis main airports to depart from

St. Louis Lambert International (STL)

Cheapest

St. Louis Lambert International is a convenient departure airport for flights to Chicago.

📍 ~20 km from St. Louis city center (reachable by car).

💸 Flights from ~$116

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient and often more affordable option for flights to Chicago.

📍 ~14 km from Chicago (reachable by car)

💸 Flights from ~$116

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by train or car), requires travel across state lines into Wisconsin.

💸 Flights from ~$237

Business & First Class Flight Deals to Chicago

30% AI deal score

$1,846

From STL

Elite

Sep 04

Chicago, United States

29% AI deal score

$2,116

From STL

Elite

Sep 05

Chicago, United States

28% AI deal score

$1,626

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from St. Louis to Chicago is typically 14-27 days before departure. During this period, the average price for a ticket is around $246. Booking too far in advance or too close to the departure date can result in higher fares. For example, flights booked 7-13 days out have an average price of $625, while those booked 0-6 days out average $468.

Across the trailing quarter, a good price for a flight from St. Louis to Chicago is considered to be $220 or less. The median price for this route has been $407. Prices can vary significantly, with some fares reaching up to $760. Therefore, if you find a ticket for $220, it is historically a favorable deal.

Historically, January and February have offered the cheapest flights from St. Louis to Chicago, with a median price of $169 for both months. May also presents a relatively lower median price at $249. The annual median price for this route is $407, indicating that these months provide significant savings compared to the yearly average.

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Flights to Chicago from other cities

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St. Louis to Chicago: Overview

Insights for flights from St. Louis to Chicago

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

Regular price: $126 - $242

Prices for flights from St. Louis to Chicago are currently below the regular range.

The regular price range for flights from St. Louis to Chicago is between $126 and $242. The current lowest deal is $117 on Kayak for travel from Sep 5-Sep 7.

now $117

Low $126

High $242

The cheapest time to fly from St. Louis to Chicago

January

Cheapest

Flights from $169

December

Most Expensive

Flights from $782

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec