September is one of the best times of the year to fly to Chicago Midway Airport from Milwaukee. Prices for September average $227 per person but you can even find prices for as low as $138. The most expensive prices can be found in the month of February. Opting for a September flight can save you 121% on your journey compared to booking in February
When flying from Milwaukee to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$592 - $874
Route
Depart
Return
Price
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Thu 5/30
1 stop11h 58m
Chicago Midway
Sun 6/2
1 stop11h 10m
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Thu 5/30
1 stop11h 07m
Chicago Midway
Sun 6/2
2 stops16h 21m
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sat 5/18
1 stop17h 17m
Chicago Midway
Tue 5/21
2 stops12h 40m
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sat 5/18
2 stops9h 13m
Chicago Midway
Tue 5/21
2 stops12h 40m
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sat 5/18
1 stop17h 17m
Chicago Midway
Tue 5/21
1 stop7h 57m
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sat 5/18
1 stop17h 17m
Chicago Midway
Tue 5/21
1 stop7h 57m
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sat 5/18
2 stops9h 13m
Chicago Midway
Tue 5/21
1 stop12h 26m
Milwaukee-MitchellChicago Midway
MKE - MDW
MKEMDW
Milwaukee-Mitchell
Sat 5/18
2 stops9h 13m
Chicago Midway
Tue 5/21
2 stops12h 40m
No data available for this route at this time. Please check back soon.
Food
Comfort
Entertainment
Crew
Overall
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Comfort
Entertainment
Crew
Overall
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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