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Cheap flights from Simpson Bay to Chicago from $211

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Simpson Bay to Chicago departing on 5/28. 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 Simpson Bay to Chicago

Cheap round-trip flights

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
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$411Spirit Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
7:07 pm - 1:42 pm
ORD
-
SXM
17h 35m
1 stop
$425Multiple Airlines
Sat, Jun 13 - Sat, Jun 20
Frontier Logo
12:43 pm - 11:19 pm
SXM
-
ORD
11h 36m
1 stop
Frontier Logo
5:25 pm - 11:23 am
ORD
-
SXM
16h 58m
1 stop
$463Frontier
Sat, Jun 20 - Fri, Jun 26
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Spirit Airlines Logo
5:10 am - 1:30 pm
ORD
-
SXM
7h 20m
1 stop
$474Spirit Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:10 am - 10:25 am
ORD
-
SXM
28h 15m
3 stops
$488Multiple Airlines
Sat, Jun 13 - Sat, Jun 20
Multiple Airlines Logo
11:30 am - 11:56 pm
SXM
-
ORD
13h 26m
2 stops
Multiple Airlines Logo
5:10 am - 1:30 pm
ORD
-
SXM
7h 20m
1 stop
$500Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
Southwest Logo
8:50 pm - 1:25 pm
MDW
-
SXM
15h 35m
2 stops
$647Southwest
Thu, May 28 - Thu, Jun 4
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
2 stops
Southwest Logo
8:50 pm - 1:25 pm
MDW
-
SXM
15h 35m
2 stops
$695Southwest
Thu, Jul 16 - Thu, Jul 23
Delta Logo
3:20 pm - 10:15 pm
SXM
-
MDW
7h 55m
1 stop
Delta Logo
6:00 am - 1:55 pm
MDW
-
SXM
6h 55m
1 stop
$740Delta
Tue, Jul 14 - Mon, Jul 20
Delta Logo
3:20 pm - 10:15 pm
SXM
-
MDW
7h 55m
1 stop
Delta Logo
6:58 pm - 1:55 pm
MDW
-
SXM
17h 57m
2 stops
$755Delta
Tue, Jul 14 - Mon, Jul 20

Spirit Airlines flights from Simpson Bay to Chicago

Our best Spirit Airlines deals on Simpson Bay to Chicago flight tickets
Spirit Airlines
May 28
SXM2:35 pmSimpson Bay Princess Juliana
9h 40m
1 stop
ORD11:15 pmChicago O'Hare Intl
Jun 4
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
$411
Spirit Airlines
Jun 11
SXM2:35 pmSimpson Bay Princess Juliana
9h 40m
1 stop
ORD11:15 pmChicago O'Hare Intl
Jun 18
ORD5:10 amChicago O'Hare Intl
7h 20m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
$474
Spirit Airlines
May 28
SXM2:35 pmSimpson Bay Princess Juliana
32h 39m
3 stops
ORD10:14 pmChicago O'Hare Intl
Jun 4
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
$512

American Airlines flights from Simpson Bay to Chicago

Our best American Airlines deals on Simpson Bay to Chicago flight tickets
American Airlines
Jul 2
SXM4:45 pmSimpson Bay Princess Juliana
14h 45m
2 stops
ORD6:30 amChicago O'Hare Intl
Jul 7
ORD5:10 amChicago O'Hare Intl
9h 32m
2 stops
SXM3:42 pmSimpson Bay Princess Juliana
$670
American Airlines
Jun 10
SXM4:43 pmSimpson Bay Princess Juliana
15h 14m
2 stops
ORD6:57 amChicago O'Hare Intl
Jun 17
ORD5:10 amChicago O'Hare Intl
9h 32m
2 stops
SXM3:42 pmSimpson Bay Princess Juliana
$675
American Airlines
May 28
SXM2:53 pmSimpson Bay Princess Juliana
10h 06m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 4
ORD9:26 pmChicago O'Hare Intl
14h 14m
1 stop
SXM12:40 pmSimpson Bay Princess Juliana
$727

momondo Fare Finder

 
Customize your flight search to find flights from Simpson Bay 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 May 1, 2026.
Use the filters below to find and compare flights from Simpson Bay to Chicago 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

Thu 5/28

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 6/4

5:05 am-1:30 pm

1 stop7h 25m

$411

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/20

7:07 pm-1:42 pm

1 stop17h 35m

$425

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/20

12:43 pm-11:19 pm

1 stop11h 36m

Chicago O'Hare Intl

Fri 6/26

5:25 pm-11:23 am

1 stop16h 58m

$463

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/11

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 6/18

5:10 am-1:30 pm

1 stop7h 20m

$474

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/20

5:10 am-10:25 am

3 stops28h 15m

$488

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/11

11:30 am-11:56 pm

2 stops13h 26m

Chicago O'Hare Intl

Thu 6/18

5:10 am-1:30 pm

1 stop7h 20m

$500

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 5/28

2:25 pm-7:10 am

2 stops17h 45m

Chicago Midway

Thu 6/4

8:50 pm-1:25 pm

2 stops15h 35m

$647

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 7/16

2:25 pm-12:15 am

2 stops10h 50m

Chicago Midway

Thu 7/23

8:50 pm-1:25 pm

2 stops15h 35m

$695
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 7/14

3:20 pm-10:15 pm

1 stop7h 55m

Chicago Midway

Mon 7/20

6:00 am-1:55 pm

1 stop6h 55m

$740

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 7/14

3:20 pm-10:15 pm

1 stop7h 55m

Chicago Midway

Mon 7/20

6:58 pm-1:55 pm

2 stops17h 57m

$755

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

Can stopping save me money on Simpson Bay to Chicago flights?

You could potentially save up to 54% on your flight if you consider stops on a Simpson Bay to Chicago flight.

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

Fastest flight time

9h 40m

Direct flights

Mon

Airports in Chicago

3 airports
The fastest flight from Simpson Bay to Chicago takes 9h 40m
Direct flights go from Simpson Bay to Chicago on Monday. 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 9h 40m.

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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

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