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Cheap flights from Simpson Bay to Chicago from $191

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Simpson Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
2:40 pm - 12:07 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
22h 27m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$367Air Canada
Sat, Oct 31 - Sat, Nov 7
Air Canada Logo
2:40 pm - 10:23 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
20h 43m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$376Air Canada
Sat, Oct 31 - Sat, Nov 7
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
9:21 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 24m1 stop Toronto Pearson Intl
$400Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
9:21 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 24m1 stop Toronto Pearson Intl
$401Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
10:15 am - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
27h 30m1 stop Toronto Pearson Intl
$403Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
46h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$406Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Air Canada Logo
3:45 pm - 1:13 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
22h 28m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 05m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$422Air Canada
Fri, Oct 30 - Fri, Nov 6
Air Canada Logo
3:45 pm - 11:07 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
20h 22m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:40 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 05m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$425Air Canada
Fri, Oct 30 - Fri, Nov 6
Air Canada Logo
3:45 pm - 9:23 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
19h 38m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
4:30 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
21h 15m1 stop Toronto Pearson Intl
$431Air Canada
Sat, Nov 7 - Sat, Nov 14
Air Canada Logo
3:45 pm - 9:23 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
19h 38m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$434Air Canada
Sat, Nov 7 - Sat, Nov 14

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Air Canada flights from Simpson Bay to Chicago

Our best Air Canada deals on Simpson Bay to Chicago flight tickets
Air Canada
Oct 31
SXM2:40 pmSimpson Bay Princess Juliana
22h 27m
1 stop
ORD12:07 pmChicago O'Hare Intl
Nov 7
ORD3:45 pmChicago O'Hare Intl
22h 00m
2 stops
SXM3:45 pmSimpson Bay Princess Juliana
$367
Air Canada
Oct 31
SXM2:40 pmSimpson Bay Princess Juliana
20h 43m
2 stops
ORD10:23 amChicago O'Hare Intl
Nov 7
ORD3:45 pmChicago O'Hare Intl
22h 00m
2 stops
SXM3:45 pmSimpson Bay Princess Juliana
$376
Air Canada
Oct 30
SXM3:45 pmSimpson Bay Princess Juliana
22h 28m
1 stop
ORD1:13 pmChicago O'Hare Intl
Nov 6
ORD8:40 pmChicago O'Hare Intl
16h 05m
2 stops
SXM2:45 pmSimpson Bay Princess Juliana
$422

American Airlines flights from Simpson Bay to Chicago

Our best American Airlines deals on Simpson Bay to Chicago flight tickets
American Airlines
Dec 2
SXM5:33 pmSimpson Bay Princess Juliana
15h 53m
2 stops
ORD7:26 amChicago O'Hare Intl
Dec 7
ORD5:00 amChicago O'Hare Intl
9h 31m
1 stop
SXM4:31 pmSimpson Bay Princess Juliana
$491
American Airlines
Oct 29
SXM4:39 pmSimpson Bay Princess Juliana
15h 48m
2 stops
ORD7:27 amChicago O'Hare Intl
Nov 6
ORD5:00 amChicago O'Hare Intl
7h 26m
1 stop
SXM2:26 pmSimpson Bay Princess Juliana
$591
American Airlines
Nov 7
SXM4:20 pmSimpson Bay Princess Juliana
9h 41m
1 stop
ORD12:01 amChicago O'Hare Intl
Nov 14
ORD5:00 amChicago O'Hare Intl
9h 31m
1 stop
SXM4:31 pmSimpson Bay Princess Juliana
$623

momondo Fare Finder

 
Use the filters below to find and compare flights from Simpson Bay to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-12:07 pm

1 stop22h 27m

Chicago O'Hare Intl

Sat 11/7

3:45 pm-3:45 pm

2 stops22h 00m

$367

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-10:23 am

2 stops20h 43m

Chicago O'Hare Intl

Sat 11/7

3:45 pm-3:45 pm

2 stops22h 00m

$376
Quickest round-trip

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 11/7

4:16 pm-11:55 pm

1 stop9h 39m

Chicago O'Hare Intl

Sat 11/14

9:21 pm-3:45 pm

1 stop16h 24m

$400

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 11/7

4:16 pm-11:55 pm

1 stop9h 39m

Chicago O'Hare Intl

Sat 11/14

9:21 pm-3:45 pm

1 stop16h 24m

$401

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 11/7

4:16 pm-11:55 pm

1 stop9h 39m

Chicago O'Hare Intl

Sat 11/14

10:15 am-3:45 pm

1 stop27h 30m

$403

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 11/7

4:16 pm-11:55 pm

1 stop9h 39m

Chicago O'Hare Intl

Sat 11/14

3:45 pm-3:45 pm

2 stops46h 00m

$406

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 10/30

3:45 pm-1:13 pm

1 stop22h 28m

Chicago O'Hare Intl

Fri 11/6

8:40 pm-2:45 pm

2 stops16h 05m

$422

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 10/30

3:45 pm-11:07 am

2 stops20h 22m

Chicago O'Hare Intl

Fri 11/6

8:40 pm-2:45 pm

2 stops16h 05m

$425

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 11/7

3:45 pm-9:23 am

2 stops19h 38m

Chicago O'Hare Intl

Sat 11/14

4:30 pm-3:45 pm

1 stop21h 15m

$431

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Sat 11/7

3:45 pm-9:23 am

2 stops19h 38m

Chicago O'Hare Intl

Sat 11/14

3:45 pm-3:45 pm

2 stops22h 00m

$434

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 Simpson Bay 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 Simpson Bay Princess Juliana to Chicago flight route?

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

What cabin class options are available on Simpson Bay to Chicago flights?

There is only 1 cabin class available to choose from on Simpson Bay 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 Simpson Bay to Chicago flights?

You could potentially save up to 29% on your flight if you consider stops on a Simpson Bay to Chicago flight.

How have Simpson Bay to Chicago flight prices changed over time?

When to book flights from Simpson Bay to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Simpson Bay to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Simpson Bay to Chicago (SXM to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Simpson Bay to Chicago

Best Price Found

$191

Fastest flight time

6h 01m

Direct flights

Mon, Fri and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Simpson Bay in the past 72 hours is $191. The best round-trip flight deal from Simpson Bay to Chicago found on momondo in the last 72 hours is $367.
The fastest flight from Simpson Bay to Chicago takes 6h 01m
Direct flights go from Simpson Bay to Chicago on Monday, Friday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Simpson Bay there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Simpson Bay to Chicago

  • How far is Simpson Bay Princess Juliana to Chicago by plane?

    Chicago is 2188.1 mi away from Simpson Bay Princess Juliana. By plane, this route typically takes 6h 01m.

  • When did momondo last update prices for flights from Simpson Bay Princess Juliana Airport to Chicago?

    Prices for flights from Simpson Bay Princess Juliana Airport to Chicago were last updated today.

  • How old do you have to be to fly from Simpson Bay Princess Juliana Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Simpson Bay Princess Juliana Airport 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 Simpson Bay to Chicago?

Traveling to a place near Chicago?

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

Why use momondo?

Why should I use momondo to find a flight deal from Simpson Bay to Chicago?

It is quick and easy to find Simpson Bay to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Simpson Bay to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Simpson Bay which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Simpson Bay to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Simpson Bay to Chicago.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Simpson Bay and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport