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Cheap flights from Simpson Bay to Chicago from $185

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 12/13. 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

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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.
Delta Logo
4:30 pm - 9:55 amSXM-ORD
19h 25m1 stop
Delta Logo
8:02 pm - 2:55 pmORD-SXM
16h 53m1 stop
$365Delta
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Sat, Nov 22 - Sat, Nov 29
Spirit Airlines Logo
3:20 pm - 9:01 amSXM-ORD
19h 41m2 stops
Spirit Airlines Logo
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
$397Spirit Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
Lufthansa Logo
2:40 pm - 6:40 pmSXM-ORD
6h 00mnonstop
Lufthansa Logo
8:45 am - 3:57 pmORD-SXM
5h 12mnonstop
$409Lufthansa
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Sat, Nov 22 - Sat, Nov 29
Lufthansa Logo
5:00 pm - 11:43 pmSXM-ORD
8h 43m1 stop
Lufthansa Logo
8:45 am - 3:57 pmORD-SXM
5h 12mnonstop
$420Lufthansa
Find Deal
Sat, Nov 22 - Sat, Nov 29
Multiple Airlines Logo
3:40 pm - 11:18 amSXM-ORD
21h 38m1 stop
Multiple Airlines Logo
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
$488Multiple Airlines
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Sat, Nov 22 - Sat, Nov 29
United Airlines Logo
2:52 pm - 11:13 pmSXM-ORD
10h 21m1 stop
United Airlines Logo
6:25 pm - 1:50 pmORD-SXM
17h 25m1 stop
$509United Airlines
Find Deal
Sat, Feb 14 - Sat, Feb 21
Multiple Airlines Logo
3:20 pm - 12:09 amSXM-ORD
10h 49m1 stop
Multiple Airlines Logo
9:34 am - 10:25 amORD-SXM
22h 51m2 stops
$516Multiple Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 24
United Airlines Logo
4:55 pm - 7:38 amSXM-ORD
16h 43m1 stop
United Airlines Logo
9:05 pm - 12:50 pmORD-SXM
14h 45m1 stop
$587United Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
5:05 pm - 11:40 pmSXM-ORD
8h 35m1 stop
American Airlines Logo
5:00 am - 4:22 pmORD-SXM
9h 22m1 stop
$625American Airlines
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Sat, Nov 22 - Sat, Nov 29
American Airlines Logo
3:00 pm - 6:54 pmSXM-ORD
5h 54mnonstop
American Airlines Logo
6:48 pm - 2:19 pmORD-SXM
17h 31m1 stop
$629American Airlines
Find Deal
Sat, Feb 14 - Sat, Feb 21

Delta flights from Simpson Bay to Chicago

Our best Delta deals on Simpson Bay to Chicago flight tickets
Delta
Nov 22
SXM4:30 pmSimpson Bay Princess Juliana
19h 25m
1 stop
ORD9:55 amChicago O'Hare Intl
Nov 29
ORD8:02 pmChicago O'Hare Intl
16h 53m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
$365
Find similar
Delta
Mar 6
SXM4:26 pmSimpson Bay Princess Juliana
24h 59m
2 stops
MDW3:25 pmChicago Midway
Mar 10
MDW5:59 pmChicago Midway
16h 16m
2 stops
SXM11:15 amSimpson Bay Princess Juliana
$632
Find similar
Delta
Mar 6
SXM4:26 pmSimpson Bay Princess Juliana
24h 57m
2 stops
MDW3:23 pmChicago Midway
Mar 10
MDW9:20 amChicago Midway
24h 55m
2 stops
SXM11:15 amSimpson Bay Princess Juliana
$722
Find similar

Spirit Airlines flights from Simpson Bay to Chicago

Our best Spirit Airlines deals on Simpson Bay to Chicago flight tickets
Spirit Airlines
Nov 22
SXM3:20 pmSimpson Bay Princess Juliana
19h 41m
2 stops
ORD9:01 amChicago O'Hare Intl
Nov 29
ORD5:00 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
$397
Find similar
Spirit Airlines
Nov 22
SXM3:20 pmSimpson Bay Princess Juliana
27h 51m
3 stops
ORD5:11 pmChicago O'Hare Intl
Nov 29
ORD5:00 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
$419
Find similar
Spirit Airlines
Nov 22
SXM3:20 pmSimpson Bay Princess Juliana
25h 28m
3 stops
ORD2:48 pmChicago O'Hare Intl
Nov 29
ORD5:00 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
$426
Find similar

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 November 3, 2025.
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

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

4:30 pm-9:55 am

1 stop19h 25m

Chicago O'Hare Intl

Sat 11/29

8:02 pm-2:55 pm

1 stop16h 53m

$365

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

3:20 pm-9:01 am

2 stops19h 41m

Chicago O'Hare Intl

Sat 11/29

5:00 am-2:15 pm

1 stop7h 15m

$397

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

2:40 pm-6:40 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

$409

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

5:00 pm-11:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

$420

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

3:40 pm-11:18 am

1 stop21h 38m

Chicago O'Hare Intl

Sat 11/29

5:00 am-2:15 pm

1 stop7h 15m

$488

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

2:52 pm-11:13 pm

1 stop10h 21m

Chicago O'Hare Intl

Sat 2/21

6:25 pm-1:50 pm

1 stop17h 25m

$509

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 12/17

3:20 pm-12:09 am

1 stop10h 49m

Chicago O'Hare Intl

Wed 12/24

9:34 am-10:25 am

2 stops22h 51m

$516

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/6

4:55 pm-7:38 am

1 stop16h 43m

Chicago O'Hare Intl

Tue 3/10

9:05 pm-12:50 pm

1 stop14h 45m

$587

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

5:05 pm-11:40 pm

1 stop8h 35m

Chicago O'Hare Intl

Sat 11/29

5:00 am-4:22 pm

1 stop9h 22m

$625

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

3:00 pm-6:54 pm

Nonstop5h 54m

Chicago O'Hare Intl

Sat 2/21

6:48 pm-2:19 pm

1 stop17h 31m

$629

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Simpson Bay to Chicago for around $773.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Simpson Bay to Chicago during this time can be as low as $452. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $614.

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 Princess Juliana to Chicago flights?

There are 3 cabin classes available to choose from on Simpson Bay Princess Juliana 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 5% 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

5h 39m

Direct flights

Mon and Sun

Airports in Chicago

1 airport
The fastest flight from Simpson Bay to Chicago takes 5h 39m
Direct flights go from Simpson Bay to Chicago on Monday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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  • 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 5h 54m.

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