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Cheap flights from St. Maarten to Chicago from $174

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from St. Maarten to Chicago departing on 9/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from St. Maarten to Chicago

Recent round-trip flight deals from St. Maarten to Chicago

Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$321Spirit Airlines
Find Deal
Sat, Sep 6 - Mon, Sep 22
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$347Spirit Airlines
Find Deal
Sat, Oct 4 - Sat, Oct 11
Spirit Airlines Logo
3:05 pm - 10:52 amSXM-ORD
20h 47m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$363Spirit Airlines
Find Deal
Mon, Oct 6 - Sat, Oct 11
JetBlue Logo
1:29 pm - 4:41 pmSXM-ORD
28h 12m1 stop
JetBlue Logo
8:34 am - 1:15 pmORD-SXM
27h 41m1 stop
$470JetBlue
Find Deal
Sat, Aug 30 - Sat, Sep 6
JetBlue Logo
1:29 pm - 7:55 amSXM-ORD
19h 26m1 stop
JetBlue Logo
8:34 am - 1:15 pmORD-SXM
27h 41m1 stop
$485JetBlue
Find Deal
Sat, Aug 30 - Sat, Sep 6
Logo
3:05 pm - 7:42 pmSXM-ORD
29h 37m3 stops
Logo
11:57 am - 11:26 amORD-SXM
22h 29m3 stops
$543
Find Deal
Sat, Aug 30 - Sat, Sep 6
Logo
3:05 pm - 10:42 amSXM-ORD
20h 37m2 stops
Logo
5:05 am - 10:45 amORD-SXM
28h 40m3 stops
$566
Find Deal
Sat, Sep 6 - Mon, Sep 22
Air Canada Logo
3:40 pm - 3:10 pmSXM-ORD
25h 30m2 stops
Air Canada Logo
1:59 pm - 4:00 pmORD-SXM
48h 01m2 stops
$586Air Canada
Find Deal
Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
2:20 pm - 10:26 pmSXM-ORD
9h 06m1 stop
American Airlines Logo
5:00 am - 1:19 pmORD-SXM
7h 19m1 stop
$587American Airlines
Find Deal
Wed, Sep 17 - Wed, Sep 24
American Airlines Logo
2:20 pm - 11:49 pmSXM-ORD
10h 29m1 stop
American Airlines Logo
8:30 pm - 1:19 pmORD-SXM
15h 49m2 stops
$592American Airlines
Find Deal
Thu, Sep 18 - Mon, Sep 22

Spirit Airlines flights from St. Maarten to Chicago

Our best Spirit Airlines deals on St. Maarten to Chicago flight tickets
Spirit Airlines
Sep 6
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 22
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$321
Find similar
Spirit Airlines
Oct 4
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 11
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$347
Find similar
Spirit Airlines
Oct 6
SXM3:05 pmSimpson Bay Princess Juliana
20h 47m
1 stop
ORD10:52 amChicago O'Hare Intl
Oct 11
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$363
Find similar

JetBlue flights from St. Maarten to Chicago

Our best JetBlue deals on St. Maarten to Chicago flight tickets
JetBlue
Aug 30
SXM1:29 pmSimpson Bay Princess Juliana
28h 12m
1 stop
ORD4:41 pmChicago O'Hare Intl
Sep 6
ORD8:34 amChicago O'Hare Intl
27h 41m
1 stop
SXM1:15 pmSimpson Bay Princess Juliana
$470
Find similar
JetBlue
Aug 30
SXM1:29 pmSimpson Bay Princess Juliana
19h 26m
1 stop
ORD7:55 amChicago O'Hare Intl
Sep 6
ORD8:34 amChicago O'Hare Intl
27h 41m
1 stop
SXM1:15 pmSimpson Bay Princess Juliana
$485
Find similar
JetBlue
Oct 5
SXM2:35 pmSimpson Bay Princess Juliana
22h 35m
1 stop
ORD12:10 pmChicago O'Hare Intl
Oct 12
ORD6:45 amChicago O'Hare Intl
29h 30m
1 stop
SXM1:15 pmSimpson Bay Princess Juliana
$530
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from St. Maarten to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 5, 2025.
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 9/22

5:05 am-2:00 pm

1 stop7h 55m

$321

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Sat 10/11

5:05 am-2:00 pm

1 stop7h 55m

$347

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 10/6

3:05 pm-10:52 am

1 stop20h 47m

Chicago O'Hare Intl

Sat 10/11

5:05 am-2:00 pm

1 stop7h 55m

$363

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/30

1:29 pm-4:41 pm

1 stop28h 12m

Chicago O'Hare Intl

Sat 9/6

8:34 am-1:15 pm

1 stop27h 41m

$470

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/30

1:29 pm-7:55 am

1 stop19h 26m

Chicago O'Hare Intl

Sat 9/6

8:34 am-1:15 pm

1 stop27h 41m

$485

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/30

3:05 pm-7:42 pm

3 stops29h 37m

Chicago O'Hare Intl

Sat 9/6

11:57 am-11:26 am

3 stops22h 29m

$543

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

Mon 9/22

5:05 am-10:45 am

3 stops28h 40m

$566

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

3:40 pm-3:10 pm

2 stops25h 30m

Chicago O'Hare Intl

Sat 12/13

1:59 pm-4:00 pm

2 stops48h 01m

$586

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 9/17

2:20 pm-10:26 pm

1 stop9h 06m

Chicago O'Hare Intl

Wed 9/24

5:00 am-1:19 pm

1 stop7h 19m

$587

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 9/18

2:20 pm-11:49 pm

1 stop10h 29m

Chicago O'Hare Intl

Mon 9/22

8:30 pm-1:19 pm

2 stops15h 49m

$592

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from St. Maarten to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $372. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from St. Maarten to Chicago for around $773.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from St. Maarten to Chicago during this time can be as low as $614. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $735.

What is the cheapest St. Maarten to Chicago flight route?

Fly from Simpson Bay Princess Juliana to Chicago O'Hare Intl for the best St. Maarten - Chicago flight prices

What cabin class options are available on St. Maarten to Chicago flights?

There are 3 cabin classes available to choose from on St. Maarten to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on St. Maarten to Chicago flights?

You could potentially save up to 33% on your flight if you consider stops on a St. Maarten to Chicago flight.

Cheap St. Maarten to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from St. Maarten to Chicago

Best Price Found

$174

Fastest flight time

5h 54m

Direct flights

Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from St. Maarten in the past 72 hours is $174. The best round-trip flight deal from St. Maarten to Chicago found on momondo in the last 72 hours is $321.
The fastest flight from St. Maarten to Chicago takes 5h 54m
Direct flights go from St. Maarten to Chicago on Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • When did momondo last update prices for flights from St. Maarten to Chicago?

    Prices for flights from St. Maarten to Chicago were last updated today.

  • How many operators does momondo search for flights from St. Maarten to Chicago?

  • How old do you have to be to fly from St. Maarten to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from St. Maarten to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from St. Maarten to Chicago?

Best airlines flying from St. Maarten to Chicago

Compare and see reviews for airlines that fly from St. Maarten to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $554Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from St. Maarten to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from St. Maarten to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from St. Maarten to Chicago with flexible booking policies on momondo?

All flight searches from St. Maarten to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from St. Maarten to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from St. Maarten.

I’m not ready to book a flight from St. Maarten to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for St. Maarten to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport