Use the Orange Line for a quick, affordable trip to MDW. It operates nearly 24 hours, reaching downtown in under 30 minutes.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $144 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | November |
Cheapest in | October |
Average price | $204 |
Good round-trip deal | $279 or less |
Good one-way deal | $98 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Mon 2/23
5:50 am-7:10 am
Nonstop1h 20m
Lambert-St Louis
Tue 2/24
6:05 am-7:15 am
Nonstop1h 10m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Tue 1/20
9:50 am-2:38 pm
1 stop4h 48m
Lambert-St Louis
Tue 1/27
7:10 am-11:59 am
1 stop4h 49m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Thu 1/8
6:10 am-2:48 pm
1 stop8h 38m
Lambert-St Louis
Mon 1/12
8:50 am-11:09 pm
1 stop14h 19m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Wed 1/7
9:32 am-4:45 pm
2 stops7h 13m
Lambert-St Louis
Wed 1/14
6:10 am-1:09 pm
1 stop6h 59m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Thu 1/8
9:55 am-11:15 am
Nonstop1h 20m
Lambert-St Louis
Mon 1/12
5:55 pm-7:05 pm
Nonstop1h 10m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Thu 2/19
5:50 am-7:10 am
Nonstop1h 20m
Lambert-St Louis
Sat 2/21
6:10 am-7:20 am
Nonstop1h 10m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Sat 1/17
6:40 am-8:05 am
Nonstop1h 25m
Lambert-St Louis
Sat 1/17
10:25 am-11:35 am
Nonstop1h 10m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Tue 2/17
3:10 pm-8:05 pm
1 stop4h 55m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Tue 1/6
7:05 am-1:35 pm
1 stop6h 30m
ChicagoSt. Louis
MDW - STL
MDWSTL
Chicago Midway
Tue 3/3
8:10 am-12:45 pm
1 stop4h 35m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
Unlike in the morning, when flights are generally more expensive, you can save up to 34% on flights from Chicago Midway Airport to St. Louis by exploring options for tickets in the afternoon.
Travelers seeking maximum savings on their Chicago Midway Airport to St. Louis flight should consider departing on Thursday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
About 11% of weekly flights between Chicago and St. Louis have experienced delays in the past year, with the average delay time being 101 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 11% of flights being delayed.
Boarding
Food
Entertainment
Crew
Comfort
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Entertainment
Crew
Comfort
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$387 | FlexibilityNo cancel fee | On-time63% |