Southwest Airlines
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United States
Gerald R. Ford International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Grand Rapids to Chicago. The full flight schedule below gives an overview of all non-stop flights from GRR to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Grand Rapids GRR to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their GRR MDW flight schedule.
Flights from GRR to MDW are operated 19 times a week, with an average of 3 flights per day. Departure times vary between 06:30 - 18:00. The earliest flight departs at 06:30, the last flight departs at 18:00. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Grand Rapids to Chicago takes 1 hour and 5 minutes. The flight distance between Grand Rapids and Chicago is 136 miles (or 219 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 19 flights per week flying from Grand Rapids to Chicago (as of April 2026).
1 hour and 5 minutes is the average flight time from Grand Rapids to Chicago.
The distance from Grand Rapids to Chicago is 136 miles (219 kilometers).
Southwest Airlines is the only airline flying nonstop from Grand Rapids to Chicago.
There are no alliances flying direct from Grand Rapids to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Grand Rapids to Chicago:
The earliest flight departs at 06:30 from Grand Rapids and arrives at 06:35 at Chicago.
The latest flight departs at 18:00 from Grand Rapids and arrives at 18:05 at Chicago.
136 miles (219 km) · 1h 5m
06:30
06:35
Southwest Airlines
WN 2237
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
06:35
06:40
Southwest Airlines
WN 3238
Southwest Airlines
Boeing 757
Y
W
J
F
06:40
06:45
Southwest Airlines
WN 3238
Southwest Airlines
Boeing 757
Y
W
J
F
06:40
06:40
Southwest Airlines
WN 2237
Southwest Airlines
Boeing 757
Y
W
J
F
06:45
06:45
Southwest Airlines
WN 2237
Southwest Airlines
Boeing 757
Y
W
J
F
09:10
09:10
Southwest Airlines
WN 2237
Southwest Airlines
Boeing 757
Y
W
J
F
12:30
12:30
Southwest Airlines
WN 4400
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:30
12:30
Southwest Airlines
WN 4375
Southwest Airlines
Boeing 757
Y
W
J
F
12:40
12:45
Southwest Airlines
WN 4400
Southwest Airlines
Boeing 757
Y
W
J
F
13:00
13:05
Southwest Airlines
WN 4375
Southwest Airlines
Boeing 757
Y
W
J
F
17:05
17:10
Southwest Airlines
WN 2194
Southwest Airlines
Boeing 757
Y
W
J
F
17:05
17:10
Southwest Airlines
WN 2194
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:40
17:45
Southwest Airlines
WN 3017
Southwest Airlines
Boeing 757
Y
W
J
F
17:40
17:45
Southwest Airlines
WN 2194
Southwest Airlines
Boeing 757
Y
W
J
F
17:45
17:50
Southwest Airlines
WN 2194
Southwest Airlines
Boeing 757
Y
W
J
F
17:50
17:55
Southwest Airlines
WN 3017
Southwest Airlines
Boeing 757
Y
W
J
F
17:50
17:55
Southwest Airlines
WN 3017
Southwest Airlines
Boeing 757
Y
W
J
F
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