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Cheap flights from Simpson Bay to Chicago from $248

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.
Copa Airlines Logo
12:20 pm - 12:11 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
13h 51m1 stop Panama City Tocumen Intl
Copa Airlines Logo
2:13 pm - 11:25 amORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
19h 12m1 stop Panama City Tocumen Intl
$448Copa Airlines
Fri, Feb 12 - Sat, Feb 20
American Airlines Logo
5:33 pm - 12:44 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 11m1 stop Miami
American Airlines Logo
6:00 am - 4:31 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
8h 31m1 stop Miami
$451American Airlines
Fri, Nov 6 - Mon, Nov 9
American Airlines Logo
5:33 pm - 7:25 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
15h 52m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
6:00 am - 4:31 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
8h 31m1 stop Miami
$456American Airlines
Fri, Nov 6 - Mon, Nov 9
Delta Logo
4:05 pm - 10:33 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 28m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 40m1 stop Atlanta Hartsfield-Jackson
$460Delta
Fri, Nov 6 - Mon, Nov 9
Delta Logo
4:05 pm - 11:57 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 52m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 2:40 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
7h 10m1 stop Atlanta Hartsfield-Jackson
$460Delta
Fri, Nov 6 - Mon, Nov 9
Delta Logo
4:05 pm - 10:33 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 28m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 40m1 stop Atlanta Hartsfield-Jackson
$468Delta
Fri, Nov 6 - Mon, Nov 9
American Airlines Logo
5:33 pm - 7:25 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
15h 52m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
9:06 pm - 2:26 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
15h 20m2 stops Charlotte Douglas Miami
$474American Airlines
Fri, Nov 6 - Mon, Nov 9
Air Canada Logo
3:45 pm - 9:08 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
19h 23m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
8:50 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 55m1 stop Toronto Pearson Intl
$479Air Canada
Sat, Dec 5 - Sat, Dec 12
Air Canada Logo
3:45 pm - 9:08 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
19h 23m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
10:57 am - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
26h 48m2 stops Ottawa Toronto Pearson Intl
$484Air Canada
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
5:33 pm - 7:25 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
15h 52m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
9:06 pm - 2:26 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
15h 20m2 stops Charlotte Douglas Miami
$527American Airlines
Fri, Nov 6 - Mon, Nov 9

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Delta flights from Simpson Bay to Chicago

Our best Delta deals on Simpson Bay to Chicago flight tickets
Delta
Nov 6
SXM4:05 pmSimpson Bay Princess Juliana
9h 52m
1 stop
ORD11:57 pmChicago O'Hare Intl
Nov 9
ORD5:30 amChicago O'Hare Intl
7h 10m
1 stop
SXM2:40 pmSimpson Bay Princess Juliana
$460
Delta
Nov 6
SXM4:05 pmSimpson Bay Princess Juliana
8h 28m
1 stop
MDW10:33 pmChicago Midway
Nov 9
MDW6:00 amChicago Midway
6h 40m
1 stop
SXM2:40 pmSimpson Bay Princess Juliana
$468
Delta
Dec 5
SXM4:10 pmSimpson Bay Princess Juliana
18h 52m
1 stop
ORD9:02 amChicago O'Hare Intl
Dec 12
ORD5:30 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:45 pmSimpson Bay Princess Juliana
$627

United Airlines flights from Simpson Bay to Chicago

Our best United Airlines deals on Simpson Bay to Chicago flight tickets
United Airlines
Dec 17
SXM2:10 pmSimpson Bay Princess Juliana
6h 01m
ORD6:11 pmChicago O'Hare Intl
Dec 23
ORD8:40 amChicago O'Hare Intl
5h 17m
SXM3:57 pmSimpson Bay Princess Juliana
$644
United Airlines
Dec 17
SXM5:00 pmSimpson Bay Princess Juliana
9h 01m
1 stop
ORD12:01 amChicago O'Hare Intl
Dec 23
ORD8:40 amChicago O'Hare Intl
5h 17m
SXM3:57 pmSimpson Bay Princess Juliana
$649
United Airlines
Dec 16
SXM2:52 pmSimpson Bay Princess Juliana
19h 00m
1 stop
ORD7:52 amChicago O'Hare Intl
Dec 23
ORD8:40 amChicago O'Hare Intl
5h 17m
SXM3:57 pmSimpson Bay Princess Juliana
$676

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

Fri 2/12

12:20 pm-12:11 am

1 stop13h 51m

Chicago O'Hare Intl

Sat 2/20

2:13 pm-11:25 am

1 stop19h 12m

$448

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-12:44 am

1 stop9h 11m

Chicago O'Hare Intl

Mon 11/9

6:00 am-4:31 pm

1 stop8h 31m

$451

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-7:25 am

2 stops15h 52m

Chicago O'Hare Intl

Mon 11/9

6:00 am-4:31 pm

1 stop8h 31m

$456
Quickest round-trip

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 11/6

4:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Mon 11/9

6:00 am-2:40 pm

1 stop6h 40m

$460

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

4:05 pm-11:57 pm

1 stop9h 52m

Chicago O'Hare Intl

Mon 11/9

5:30 am-2:40 pm

1 stop7h 10m

$460

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 11/6

4:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Mon 11/9

6:00 am-2:40 pm

1 stop6h 40m

$468

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-7:25 am

2 stops15h 52m

Chicago O'Hare Intl

Mon 11/9

9:06 pm-2:26 pm

2 stops15h 20m

$474

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Sat 12/5

3:45 pm-9:08 am

2 stops19h 23m

Chicago O'Hare Intl

Sat 12/12

8:50 pm-3:45 pm

1 stop16h 55m

$479

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Sat 12/5

3:45 pm-9:08 am

2 stops19h 23m

Chicago O'Hare Intl

Sat 12/12

10:57 am-3:45 pm

2 stops26h 48m

$484

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-7:25 am

2 stops15h 52m

Chicago O'Hare Intl

Mon 11/9

9:06 pm-2:26 pm

2 stops15h 20m

$527

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 31% 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

$248

Fastest flight time

6h 01m

Direct flights

Mon, Tue, Fri and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Simpson Bay in the past 72 hours is $248. The best round-trip flight deal from Simpson Bay to Chicago found on momondo in the last 72 hours is $448.
The fastest flight from Simpson Bay to Chicago takes 6h 01m
Direct flights go from Simpson Bay to Chicago on Monday, Tuesday, 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
Saint Joseph
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
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