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Cheap flights from St. Maarten to Chicago from $179

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 5/14. 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

Find the cheapest flights from St. Maarten to Chicago

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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Spirit Airlines Logo
6:15 am - 1:30 pm
ORD
-
SXM
30h 15m
3 stops
$382Spirit Airlines
Sat, May 9 - Fri, May 15
Multiple Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
7:52 pm - 1:30 pm
ORD
-
SXM
16h 38m
2 stops
$395Multiple Airlines
Sat, May 9 - Fri, May 15
Spirit Airlines Logo
2:35 pm - 12:04 pm
SXM
-
ORD
22h 29m
2 stops
Spirit Airlines Logo
6:15 am - 1:30 pm
ORD
-
SXM
30h 15m
3 stops
$472Spirit Airlines
Sat, May 9 - Fri, May 15
Spirit Airlines Logo
2:35 pm - 12:04 pm
SXM
-
ORD
22h 29m
3 stops
Spirit Airlines Logo
6:15 am - 1:30 pm
ORD
-
SXM
30h 15m
3 stops
$517Spirit Airlines
Sat, May 9 - Fri, May 15
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$523Spirit Airlines
Thu, Jun 4 - Thu, Jun 11
Multiple Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
7:52 pm - 1:30 pm
ORD
-
SXM
40h 38m
2 stops
$527Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Multiple Airlines Logo
9:35 am - 11:26 pm
SXM
-
ORD
14h 51m
2 stops
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$539Multiple Airlines
Wed, Jun 3 - Sun, Jun 7
Multiple Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
6:35 pm - 1:30 pm
ORD
-
SXM
41h 55m
3 stops
$541Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Multiple Airlines Logo
11:30 am - 11:56 pm
SXM
-
ORD
13h 26m
2 stops
Multiple Airlines Logo
6:35 pm - 1:30 pm
ORD
-
SXM
41h 55m
3 stops
$619Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Air Canada Logo
6:00 pm - 2:55 pm
SXM
-
ORD
21h 55m
1 stop
Air Canada Logo
2:15 pm - 5:00 pm
ORD
-
SXM
25h 45m
1 stop
$620Air Canada
Sat, May 9 - Fri, May 15

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Spirit Airlines flights from St. Maarten to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on St. Maarten to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
May 9
SXM2:35 pmSimpson Bay Princess Juliana
9h 40m
1 stop
ORD11:15 pmChicago O'Hare Intl
May 15
ORD6:15 amChicago O'Hare Intl
30h 15m
3 stops
SXM1:30 pmSimpson Bay Princess Juliana
$382
Spirit Airlines
May 9
SXM2:35 pmSimpson Bay Princess Juliana
22h 29m
2 stops
ORD12:04 pmChicago O'Hare Intl
May 15
ORD6:15 amChicago O'Hare Intl
30h 15m
3 stops
SXM1:30 pmSimpson Bay Princess Juliana
$472
Spirit Airlines
May 9
SXM2:35 pmSimpson Bay Princess Juliana
22h 29m
3 stops
ORD12:04 pmChicago O'Hare Intl
May 15
ORD6:15 amChicago O'Hare Intl
30h 15m
3 stops
SXM1:30 pmSimpson Bay Princess Juliana
$517

American Airlines flights from St. Maarten to Chicago O'Hare Intl Airport

Our best American Airlines deals on St. Maarten to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 2
SXM4:46 pmSimpson Bay Princess Juliana
17h 24m
1 stop
ORD9:10 amChicago O'Hare Intl
Jul 7
ORD6:47 pmChicago O'Hare Intl
18h 04m
1 stop
SXM1:51 pmSimpson Bay Princess Juliana
$665
American Airlines
Jul 2
SXM4:46 pmSimpson Bay Princess Juliana
15h 06m
2 stops
ORD6:52 amChicago O'Hare Intl
Jul 7
ORD5:10 amChicago O'Hare Intl
7h 41m
1 stop
SXM1:51 pmSimpson Bay Princess Juliana
$670
American Airlines
May 9
SXM2:21 pmSimpson Bay Princess Juliana
11h 04m
1 stop
ORD12:25 amChicago O'Hare Intl
May 15
ORD8:46 pmChicago O'Hare Intl
13h 51m
2 stops
SXM11:37 amSimpson Bay Princess Juliana
$839

momondo Fare Finder

 
Customize your flight search to find flights from St. Maarten to Chicago O'Hare Intl Airport 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 April 21, 2026.
Use the filters below to find and compare flights from St. Maarten to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 5/9

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/15

6:15 am-1:30 pm

3 stops30h 15m

$382

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 5/9

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/15

7:52 pm-1:30 pm

2 stops16h 38m

$395

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 5/9

2:35 pm-12:04 pm

2 stops22h 29m

Chicago O'Hare Intl

Fri 5/15

6:15 am-1:30 pm

3 stops30h 15m

$472

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 5/9

2:35 pm-12:04 pm

3 stops22h 29m

Chicago O'Hare Intl

Fri 5/15

6:15 am-1:30 pm

3 stops30h 15m

$517
Quickest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/4

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 6/11

5:05 am-1:30 pm

1 stop7h 25m

$523

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/4

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 6/11

7:52 pm-1:30 pm

2 stops40h 38m

$527

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 6/3

9:35 am-11:26 pm

2 stops14h 51m

Chicago O'Hare Intl

Sun 6/7

5:05 am-1:30 pm

1 stop7h 25m

$539

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/4

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 6/11

6:35 pm-1:30 pm

3 stops41h 55m

$541

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/4

11:30 am-11:56 pm

2 stops13h 26m

Chicago O'Hare Intl

Thu 6/11

6:35 pm-1:30 pm

3 stops41h 55m

$619

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 5/9

6:00 pm-2:55 pm

1 stop21h 55m

Chicago O'Hare Intl

Fri 5/15

2:15 pm-5:00 pm

1 stop25h 45m

$620

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 O'Hare Intl Airport

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 St. Maarten to Chicago O'Hare Intl flight route?

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

What cabin class options are available on St. Maarten to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on St. Maarten to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

You could potentially save up to 64% on your flight if you consider stops on a St. Maarten to Chicago O'Hare Intl Airport flight.

Cheap St. Maarten to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from St. Maarten to Chicago O'Hare Intl Airport

Fastest flight time

9h 19m

Direct flights

None
The fastest flight from St. Maarten to Chicago O'Hare Intl Airport takes 9h 19m
There are no direct flights from St. Maarten to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Simpson Bay Princess Juliana Airport - Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from St. Maarten to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from St. Maarten to Chicago O'Hare Intl Airport?

    Prices for flights from St. Maarten to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from St. Maarten to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from St. Maarten to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from St. Maarten to Chicago O'Hare Intl Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

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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