Travelers have found it’s best to book a flight 55 days in advance to save up to 550% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 55 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to St. Maarten 1-2 weeks in advance for as low as $464, or $841 for flights within the next 24 hours.
Due to multiple factors, expect to potentially pay more when booking in July. For low rates, September can be a great choice for travel to St. Maarten. Flights to St. Maarten from Chicago Midway Airport in September are about $739 on average during September, but can be found for as low as $481.
When flying from Chicago Midway Airport to St. Maarten, 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
$321 - $965
Route
Depart
Return
Price
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Sun 7/7
2 stops17h 18m
Simpson Bay Princess Juliana
Sat 7/13
1 stop22h 29m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Thu 5/30
2 stops41h 05m
Simpson Bay Princess Juliana
Sun 6/2
1 stop28h 47m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Thu 6/6
2 stops25h 39m
Simpson Bay Princess Juliana
Fri 6/14
2 stops17h 30m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Thu 6/6
2 stops25h 39m
Simpson Bay Princess Juliana
Mon 6/10
2 stops29h 41m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Sun 7/7
2 stops17h 18m
Simpson Bay Princess Juliana
Sat 7/13
2 stops22h 25m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Sun 6/30
2 stops19h 22m
Simpson Bay Princess Juliana
Fri 7/5
2 stops15h 16m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Tue 7/23
1 stop17h 50m
Simpson Bay Princess Juliana
Sat 8/17
2 stops18h 25m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Fri 9/27
1 stop6h 49m
Simpson Bay Princess Juliana
Mon 9/30
2 stops18h 26m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Wed 6/19
2 stops21h 48m
Simpson Bay Princess Juliana
Sun 6/23
3 stops29h 26m
No data available for this route at this time. Please check back soon.
Overall
Comfort
Entertainment
Food
Crew
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Comfort
Entertainment
Food
Crew
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Comfort
Entertainment
Food
Crew
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Comfort
Entertainment
Food
Crew
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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