Southwest offers free messaging and high-speed Wi-Fi for a fee, enhancing connectivity.
Southwest's Early Bird check-in provides priority boarding, automatically checking you in 36 hours before departure.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $139 (Southwest) |
One-way from | $64 (Priceline) |
Popular in | May |
Cheapest in | February |
Average price | $271 |
Fly from
Fly to
Route
Depart
Return
Price
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Wed 12/31
4:45 pm-5:50 pm
Nonstop2h 05m
Chicago Midway
Thu 1/1
8:50 am-1:55 pm
1 stop4h 05m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Thu 1/8
5:50 pm-7:00 pm
Nonstop2h 10m
Chicago Midway
Mon 1/12
9:50 am-12:40 pm
Nonstop1h 50m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Thu 1/22
1:45 pm-2:55 pm
Nonstop2h 10m
Chicago Midway
Sun 1/25
7:05 am-10:00 am
Nonstop1h 55m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Wed 1/7
6:00 am-8:52 am
1 stop3h 52m
Chicago Midway
Sat 1/10
11:21 am-5:46 pm
1 stop5h 25m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Thu 1/8
11:24 am-4:29 pm
1 stop6h 05m
Chicago Midway
Mon 1/12
9:32 am-4:38 pm
1 stop6h 06m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Mon 1/12
4:20 pm-6:35 pm
1 stop3h 15m
Chicago Midway
Thu 1/15
10:45 am-1:35 pm
Nonstop1h 50m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Thu 1/29
7:22 am-11:59 am
1 stop5h 37m
Chicago Midway
Sun 2/1
6:35 pm-11:05 pm
1 stop3h 30m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Fri 2/27
11:45 am-5:37 pm
1 stop6h 52m
Chicago Midway
Sun 3/1
6:40 pm-12:37 am
1 stop4h 57m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Fri 2/27
7:35 am-8:50 am
Nonstop2h 15m
Chicago Midway
Sun 3/1
6:35 pm-9:25 pm
Nonstop1h 50m
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Mon 1/26
7:45 am-9:05 am
Nonstop2h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
To ensure you get the cheapest price possible for a flight from Baltimore to Chicago Midway Airport, you should look to book at least 36 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, March is the cheapest month in which you can book a flight from Baltimore to Chicago Midway Airport (average of $49). Flying from Baltimore to Chicago Midway Airport in January is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s optimal to fly from Baltimore to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 45% on the cost of your flight, compared to a flight in the morning.
Travelers seeking maximum savings on their Baltimore to Chicago Midway Airport flight should consider departing on Monday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
About 17% of weekly flights between Baltimore and Chicago have experienced delays in the past year, with the average delay time being 119 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Thursday 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 16% of flights being delayed.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$163 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$293 | FlexibilityNo cancel fee | On-time63% |