Can I fly direct from St. Louis to Chicago?

Yes, direct flights from St. Louis to Chicago are available. Historically, approximately 25.9% of the flights on this route were direct over a 90-day period. For flights that included connections, travelers typically experienced a median of 3 stopovers. This indicates that while direct options exist, a significant portion of flights involve at least one stop.

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

The typical direct flight from St. Louis to Chicago has a median duration of 1 hour and 31 minutes. This route covers an approximate distance of 404 kilometers. For flights that include one stop, the median travel time is considerably longer, averaging 5 hours and 6 minutes. Travelers should account for these differences when planning their journey.

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

Historically, flight prices for the St. Louis to Chicago route have shown regular price drops. This indicates that travelers can typically expect opportunities to find deals on this route. The pricing trends over a 30-day window suggest a consistent pattern of price fluctuations, making it a route where monitoring prices can be beneficial for securing a good deal.

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 4 days ago

476 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Oct 12, 2026.)

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

Explore current cheapest deals departing from St. Louis to Chicago

2026-11-12 – 2026-11-13
STL - Chicago
70% AI deal score
$223
$147
Round trip
2026-11-12 – 2026-12-03
STL - Chicago
46% AI deal score
$177
$147
Round trip
2026-11-12 – 2026-12-10
STL - Chicago
42% AI deal score
$177
$161
Round trip
2026-11-12 – 2026-11-27
STL - Chicago
43% AI deal score
$182
$162
Round trip
2026-11-12 – 2026-11-18
STL - Chicago
47% AI deal score
$212
$166
Round trip
2026-11-12 – 2026-11-14
STL - Chicago
67% AI deal score
$223
$170
Round trip
2026-11-02 – 2026-11-11
STL - Chicago
75% AI deal score
$224
$171
Round trip
2026-11-21 – 2026-11-22
STL - Chicago
40% AI deal score
$123
$171
Round trip
2026-12-20 – 2026-12-22
STL - Chicago
40% AI deal score
$136
$171
Round trip
2026-12-02 – 2026-12-17
STL - Chicago
45% AI deal score
$205
$171
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 fares typically range from $330–$1473, with a median price of $716. Right now, current fares are below the typical level, which can be an opportune time to consider booking. However, the share of recent fares classified as a good price is 0%, indicating that deals are not currently abundant.

The cheapest time to fly from St. Louis to Chicago is often in February, with a median fare of $186. December also offers competitive pricing, with a median of $187. If you are planning a summer trip, July presents a median fare of $311, which is still considerably lower than the overall median.

Most itineraries for flights from St. Louis to Chicago are not direct, with only 25.9% of recent fares being non-stop. For the majority of itineraries that do connect, the typical number of stopovers is 3. This means you should account for additional travel time when planning your journey.

A typical journey from St. Louis to Chicago takes approximately 1h 27m, including connections. This median duration reflects the common travel experience, which often involves multiple stopovers given the prevalence of connecting flights on this route.

The distance between St. Louis and Chicago is approximately 404 kilometers. This classifies the route as a short-haul flight, meaning it is a relatively brief journey suitable for quick trips.

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

Regular price: $91 - $258

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

The regular price range for flights from St. Louis to Chicago is between $91 and $258. The current lowest deal is $170 with American Airlines for travel from Nov 21-Nov 22.

now $170

Low $91

High $258

The cheapest time to fly from St. Louis to Chicago

The cheapest month to fly from St. Louis to Chicago is February, with a median price of $186. The most expensive month is January, with a median price of $2033. Prices are generally lower from February to December.

February

Cheapest

Flights from $186

January

Most Expensive

Flights from $2,033

Jan

Feb

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from St. Louis to Chicago

United Airlines

Last-minute flights going from St. Louis to Chicago

Fri, Oct 9

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (ORD)

Frontier Airlines

$401

$378

One-way

Sat, Oct 10

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (MDW)

Deutsche Luft Hansa

$411

$572

One-way

Fri, Oct 16

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (MDW)

Frontier Airlines

$312

$389

One-way

Mon, Oct 19

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (ORD)

Frontier Airlines

$250

$369

One-way

Mon, Oct 19

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (MDW)

Alaska Airlines, Inc.

$145

$474

One-way

Mon, Oct 26

⌛ Last-Minute

STL - Chicago

St. Louis (STL) - Chicago (MDW)

Frontier Airlines

$211

$308

One-way

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

3 nights

Nov 6 - Nov 9

$250 → $155

38%

5 nights

Nov 4 - Nov 9

$246 → $155

37%

2 nights

Nov 16 - Nov 18

$246 → $155

37%

5 nights

Nov 6 - Nov 11

$245 → $155

37%

Popular Airports to fly from St. Louis to Chicago

St. Louis - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from St. Louis to Chicago are below the typical level at a median of $716.

📅 Best time to fly

February is historically the cheapest month

Historically, February is the cheapest month to fly from St. Louis to Chicago, with a median price of $186.

⏱️ Flight duration

Direct flights average 1h 27m

Direct flights from St. Louis to Chicago typically average 1 hour and 27 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant on this route, making up 74.1% of recent deals.

🏆 Airline highlight

American Airlines offers a recent deal

A recent deal from St. Louis to Chicago was offered by American Airlines for $170.

🎯 Booking tip

Deals appear regularly

Deals for flights from St. Louis to Chicago appear regularly, typically within a 30-day window.

St. Louis main airports to depart from

St. Louis Lambert International (STL)

Cheapest

St. Louis Lambert International is a convenient option for flights from St. Louis to Chicago.

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

💸 Flights from ~$117

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International Airport is a convenient option for flights from St. Louis to Chicago.

📍 ~14 km from Chicago city center (reachable by car)

💸 Flights from ~$117

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$308

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from St. Louis to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From STL

Elite

Jan 16

Chicago, United States

76% AI deal score

$2,007

$540

Save $1,467

From STL

Elite

Nov 11

Chicago, United States

71% AI deal score

$417

$346

Save $71

United Airlines

Business Class

From STL

Elite

Dec 09

Chicago, United States

71% AI deal score

$426

$346

Save $80

United Airlines

Business Class

From STL

Chicago, United States

48% AI deal score

$2,363

$1,941

Save $422

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal time to purchase tickets for flights from St. Louis to Chicago is typically 14-27 days before departure. During this period, the average price observed was $1431. Prices tend to increase as the departure date approaches, with flights booked 28-59 days out averaging $3246, and those booked 60+ days in advance costing an average of $5633. This trend was observed across a 90-day window of flight data.

A flight from St. Louis to Chicago is generally considered a good deal if the price is around $330 or less. This threshold represents the 25th percentile of prices observed over a 90-day period. The median price for this route was $716, while prices at the 75th percentile reached $1473. Therefore, securing a ticket at or below $330 indicates a favorable price.

Historically, February and December have offered the cheapest flights from St. Louis to Chicago, with median prices of $186 and $187, respectively. July also presented a relatively lower median price of $311. The annual median price for this route, based on a 270-day window, was $716. While July showed a lower median price among the cheapest months, it was also identified as the most expensive month overall with a median of $311.

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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: $91 - $258

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

The regular price range for flights from St. Louis to Chicago is between $91 and $258. The current lowest deal is $170 with American Airlines for travel from Nov 21-Nov 22.

now $170

Low $91

High $258

The cheapest time to fly from St. Louis to Chicago

February

Cheapest

Flights from $186

January

Most Expensive

Flights from $2,033

Jan

Feb

Jul

Aug

Sep

Oct

Nov

Dec