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Cheap flights from St. Maarten to Chicago from $206

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 3/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:25 pm - 11:59 pm
SXM
-
ORD
12h 34m
2 stops
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$345Multiple Airlines
Thu, Apr 23 - Sun, May 3
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Spirit Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
$370Spirit Airlines
Thu, Apr 23 - Sun, May 3
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
$381Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
2:00 pm - 2:55 pm
ORD
-
SXM
23h 55m
1 stop
$389Multiple Airlines
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
3:45 pm - 2:55 pm
ORD
-
SXM
22h 10m
2 stops
$393Multiple Airlines
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
1:27 pm - 1:37 pm
ORD
-
SXM
23h 10m
1 stop
$407Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
2:35 pm - 11:17 pm
SXM
-
ORD
9h 42m
1 stop
Multiple Airlines Logo
4:34 pm - 3:15 pm
ORD
-
SXM
21h 41m
1 stop
$411Multiple Airlines
Wed, Apr 8 - Fri, Apr 10
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
5:57 pm - 1:37 pm
ORD
-
SXM
42h 40m
2 stops
$419Multiple Airlines
Sat, Apr 18 - Tue, Apr 28
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
12:53 pm - 11:20 am
ORD
-
SXM
21h 27m
2 stops
$424Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
1:43 pm - 1:37 pm
ORD
-
SXM
22h 54m
1 stop
$425Multiple Airlines
Sat, Apr 18 - Fri, Apr 24

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
Apr 18
SXM2:42 pmSimpson Bay Princess Juliana
10h 42m
1 stop
ORD12:24 amChicago O'Hare Intl
Apr 25
ORD7:15 pmChicago O'Hare Intl
17h 22m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$381
Spirit Airlines
Apr 18
SXM2:42 pmSimpson Bay Princess Juliana
10h 42m
1 stop
ORD12:24 amChicago O'Hare Intl
Apr 26
ORD5:05 amChicago O'Hare Intl
7h 32m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$431
Spirit Airlines
Apr 18
SXM2:42 pmSimpson Bay Princess Juliana
20h 41m
2 stops
ORD10:23 amChicago O'Hare Intl
Apr 26
ORD5:05 amChicago O'Hare Intl
7h 32m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$458

Air Canada flights from St. Maarten to Chicago O'Hare Intl Airport

Our best Air Canada deals on St. Maarten to Chicago O'Hare Intl Airport flight tickets
Air Canada
Apr 17
SXM4:00 pmSimpson Bay Princess Juliana
27h 58m
2 stops
ORD6:58 pmChicago O'Hare Intl
Apr 26
ORD2:00 pmChicago O'Hare Intl
23h 55m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
$445
Air Canada
Apr 20
SXM4:00 pmSimpson Bay Princess Juliana
19h 53m
2 stops
ORD10:53 amChicago O'Hare Intl
Apr 26
ORD9:50 amChicago O'Hare Intl
28h 05m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
$448
Air Canada
Apr 17
SXM4:00 pmSimpson Bay Princess Juliana
16h 58m
2 stops
ORD7:58 amChicago O'Hare Intl
Apr 24
ORD6:21 pmChicago O'Hare Intl
19h 34m
2 stops
SXM2:55 pmSimpson Bay Princess Juliana
$464

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 March 3, 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

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/23

12:25 pm-11:59 pm

2 stops12h 34m

Chicago O'Hare Intl

Sun 5/3

5:05 am-1:30 pm

1 stop7h 25m

$345

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/23

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sun 5/3

5:05 am-1:37 pm

1 stop7h 32m

$370

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

7:15 pm-1:37 pm

1 stop17h 22m

$381

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/16

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Thu 4/23

2:00 pm-2:55 pm

1 stop23h 55m

$389

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/16

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Thu 4/23

3:45 pm-2:55 pm

2 stops22h 10m

$393

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

1:27 pm-1:37 pm

1 stop23h 10m

$407

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/8

2:35 pm-11:17 pm

1 stop9h 42m

Chicago O'Hare Intl

Fri 4/10

4:34 pm-3:15 pm

1 stop21h 41m

$411

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Tue 4/28

5:57 pm-1:37 pm

2 stops42h 40m

$419

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

12:53 pm-11:20 am

2 stops21h 27m

$424

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Fri 4/24

1:43 pm-1:37 pm

1 stop22h 54m

$425

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 day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Saturday is the most expensive day to depart from St. Maarten because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $610.

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 66% 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

5h 46m

Direct flights

Sun
The fastest flight from St. Maarten to Chicago O'Hare Intl Airport takes 5h 46m
Direct flights go from St. Maarten to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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
Naperville
Rosemont
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

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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