Cheap flights from St Louis to Chicago from $61 STL → MDW, ORD
Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)
The cheapest return found recently is $290 with Southwest Airlines, 13 Dec – 14 Dec, found 4 days ago. The cheapest one-way found recently is $61 with Southwest Airlines, 30 Dec, found today.
- Cheapest one-way found recently
- $61, Southwest Airlines, found today
- Cheapest return found recently
- $290, 13 Dec to 14 Dec
- Cheapest month to fly
- January 2027, one-way fares from $60 found in the last 7 days
- Airlines with nonstop flights
- American Airlines, Southwest Airlines
- Shortest nonstop flight found
- 1 h 5 min
Return
Not enough comparable prices yet for a usual return price.
Cheapest return found recently
$290
13 Dec – 14 Dec · Southwest Airlines
Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW)
Leaves 1:05 p.m. · Return leaves 11:30 a.m. · 2 h 15 min of travel, both ways together
out nonstop, back nonstop
found 4 days ago
Cheapest nonstop return
$290
13 Dec – 14 Dec · Southwest Airlines
Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW)
Leaves 1:05 p.m. · Return leaves 11:30 a.m. · 2 h 15 min of travel, both ways together
out nonstop, back nonstop
found 4 days ago
Found recently, and the cheapest we hold
$290 13 Dec – 14 Decfound 4 days agoSee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 29 days, 24 Sept to 12 Nov, the cheapest return we saw each day was $133 to $403.
29 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Not enough comparable prices yet: we hold return fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other 1-night return fares leaving within 3 days of 13 Dec to compare.
Every date we hold
1 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 13 Dec – 14 Dec | $290 | Southwest Airlines | Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
Airlines on the cheapest dates: Southwest Airlines.
One-way
The cheapest one-way fare on each of 6 departure dates is usually $73 to $167.
Cheapest one-way found recently
$61
30 Dec · Southwest Airlines
Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW)
Leaves 1:40 p.m. · 1 h 5 min trip
nonstop
found today
Cheapest nonstop one-way
$61
30 Dec · Southwest Airlines
Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW)
Leaves 1:40 p.m. · 1 h 5 min trip
nonstop
found today
Found recently, and the cheapest we hold
$61 30 Decfound todayOpen this trip
$60 9 Jan 2027found 2 days agoOpen this trip
What have prices looked like?
Over 50 days, 24 Sept to 12 Nov, the cheapest one-way we saw each day was $60 to $204.
At $61, the cheapest one-way found recently is at the low end of that range.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 6 departure dates from 17 Nov to 9 Jan 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 30 Dec to compare.
Every date we hold
6 fares on 6 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 17 Nov | $181 | American Airlines | Lambert-St. Louis International Airport (STL) → O'Hare International Airport (ORD) | nonstop | found yesterday | Open this trip |
| 19 Nov | $110 | American Airlines | Lambert-St. Louis International Airport (STL) → O'Hare International Airport (ORD) | nonstop | found 4 days ago | Open this trip |
| 22 Nov | $124 | American Airlines | Lambert-St. Louis International Airport (STL) → O'Hare International Airport (ORD) | nonstop | found yesterday | Open this trip |
| 1 Dec | $230 | Frontier Airlines | Lambert-St. Louis International Airport (STL) → O'Hare International Airport (ORD) | 2 stops | found today | Open this trip |
| 30 Dec | $61 | Southwest Airlines | Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW) | nonstop | found today | Open this trip |
| 9 Jan 2027 | $60 | Southwest Airlines | Lambert-St. Louis International Airport (STL) → Chicago Midway International Airport (MDW) | nonstop | found 2 days ago | Open this trip |
Which month looks cheapest?
January 2027 is the cheapest month — from $60.
Airlines on the cheapest dates: American Airlines, Southwest Airlines, Frontier Airlines.
Premium cabin fares from St Louis to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 13 Dec – 14 Dec in another cabin: Premium economy · Business · First
Today's prices for 30 Dec in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for St Louis to Chicago?
Return
The cheapest fares were 14 to 29 days before departure.
From the cheapest return each day between 24 Sept and 12 Nov (29 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 14–29 days | $218 | $133 | Cheapest seen | 14 |
| 90–179 days | $247 | $247 | +13% | 8 |
| 180+ days | $403 | $403 | +85% | 15 |
One-way
Fares 90 to 179 days before departure were typically 31% lower than 0 to 6 days before departure.
From the cheapest one-way each day between 24 Sept and 12 Nov (50 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $105 | $80 | +44% | 43 |
| 7–13 days | $102 | $68 | +40% | 47 |
| 14–29 days | $84 | $68 | +15% | 9 |
| 60–89 days | $74 | $62 | +1% | 17 |
| 90–179 days | $73 | $73 | Cheapest seen | 13 |
| 180+ days | $201 | $201 | +175% | 8 |
Live price for these dates
The cheapest return found recently is for 13 Dec – 14 Dec. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from St Louis to Chicago?
The cheapest return found recently is $290 with Southwest Airlines, 13 Dec to 14 Dec, found 4 days ago.
How much is a one-way flight from St Louis to Chicago?
The cheapest one-way found recently is $61 with Southwest Airlines, 30 Dec, found today. The cheapest one-way we hold, of any age, is $60 with Southwest Airlines, 9 Jan 2027, found 2 days ago. The cheapest one-way fare on each of 6 departure dates is usually $73 to $167.
What is the cheapest month to fly from St Louis to Chicago?
January 2027 is the cheapest month for a one-way, from $60, 9 Jan 2027, found 2 days ago.
How far ahead should I book a flight from St Louis to Chicago?
In 29 days of prices between 24 Sept and 12 Nov, return fares were cheapest 14 to 29 days before departure. In 50 days of prices between 24 Sept and 12 Nov, one-way fares 90 to 179 days before departure were typically 31% lower than 0 to 6 days before departure.
Is there a direct flight from St Louis to Chicago?
Yes, the cheapest nonstop return found recently is $290 with Southwest Airlines, 13 Dec to 14 Dec, found 4 days ago. The cheapest nonstop one-way found recently is $61 with Southwest Airlines, 30 Dec, found today.
How long is the flight from St Louis to Chicago?
The cheapest nonstop one-way found recently, with Southwest Airlines on 30 Dec, takes 1 h 5 min from Lambert-St. Louis International Airport (STL) to Chicago Midway International Airport (MDW).
Which airlines have the cheapest flights from St Louis to Chicago?
Between 17 Nov and 9 Jan 2027, American Airlines has the cheapest one-way on 3 of the 6 departure dates we hold, Southwest Airlines on 2 and Frontier Airlines on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work