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Cheap flights from Simpson Bay to Chicago from $200

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 10/31. 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

Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$342Spirit Airlines
Find Deal
Mon, Sep 15 - Mon, Sep 22
Spirit Airlines Logo
3:05 pm - 10:18 amSXM-ORD
20h 13m2 stops
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$443Spirit Airlines
Find Deal
Mon, Sep 15 - Mon, Sep 22
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
Spirit Airlines Logo
5:17 pm - 2:00 pmORD-SXM
19h 43m3 stops
$448Spirit Airlines
Find Deal
Fri, Sep 5 - Thu, Sep 11
JetBlue Logo
2:35 pm - 6:23 pmSXM-ORD
28h 48m1 stop
JetBlue Logo
1:35 pm - 1:15 pmORD-SXM
22h 40m1 stop
$465JetBlue
Find Deal
Fri, Sep 5 - Thu, Sep 11
Delta Logo
3:10 pm - 12:28 pmSXM-MDW
22h 18m2 stops
Delta Logo
1:08 pm - 1:50 pmMDW-SXM
23h 42m2 stops
$603Delta
Find Deal
Fri, Sep 5 - Thu, Sep 11
American Airlines Logo
2:20 pm - 7:47 amSXM-ORD
18h 27m2 stops
American Airlines Logo
9:37 pm - 1:19 pmORD-SXM
14h 42m2 stops
$617American Airlines
Find Deal
Mon, Sep 15 - Mon, Sep 22
American Airlines Logo
4:24 pm - 7:25 amSXM-ORD
16h 01m2 stops
American Airlines Logo
8:44 pm - 1:37 pmORD-SXM
15h 53m2 stops
$621American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
Delta Logo
3:10 pm - 8:35 amSXM-MDW
18h 25m2 stops
Delta Logo
12:43 pm - 1:50 pmMDW-SXM
24h 07m1 stop
$807Delta
Find Deal
Fri, Sep 5 - Thu, Sep 11
Logo
11:35 am - 5:37 pmSXM-MDW
31h 02m3 stops
Logo
5:20 pm - 10:50 amMDW-SXM
16h 30m2 stops
$1,333
Find Deal
Fri, Sep 5 - Thu, Sep 11
Logo
11:35 am - 5:37 pmSXM-MDW
31h 02m3 stops
Logo
9:20 am - 10:50 amMDW-SXM
24h 30m3 stops
$1,457
Find Deal
Fri, Sep 5 - Thu, Sep 11

Spirit Airlines flights from Simpson Bay to Chicago

Our best Spirit Airlines deals on Simpson Bay to Chicago flight tickets
Spirit Airlines
Sep 15
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 22
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$342
Find similar
Spirit Airlines
Sep 15
SXM3:05 pmSimpson Bay Princess Juliana
20h 13m
2 stops
ORD10:18 amChicago O'Hare Intl
Sep 22
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$443
Find similar
Spirit Airlines
Sep 5
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 11
ORD5:17 pmChicago O'Hare Intl
19h 43m
3 stops
SXM2:00 pmSimpson Bay Princess Juliana
$448
Find similar

American Airlines flights from Simpson Bay to Chicago

Our best American Airlines deals on Simpson Bay to Chicago flight tickets
American Airlines
Sep 15
SXM2:20 pmSimpson Bay Princess Juliana
18h 27m
2 stops
ORD7:47 amChicago O'Hare Intl
Sep 22
ORD9:37 pmChicago O'Hare Intl
14h 42m
2 stops
SXM1:19 pmSimpson Bay Princess Juliana
$617
Find similar
American Airlines
Oct 9
SXM4:24 pmSimpson Bay Princess Juliana
16h 01m
2 stops
ORD7:25 amChicago O'Hare Intl
Oct 15
ORD8:44 pmChicago O'Hare Intl
15h 53m
2 stops
SXM1:37 pmSimpson Bay Princess Juliana
$621
Find similar
American Airlines
Oct 9
SXM4:24 pmSimpson Bay Princess Juliana
17h 29m
1 stop
ORD8:53 amChicago O'Hare Intl
Oct 15
ORD5:05 pmChicago O'Hare Intl
21h 10m
1 stop
SXM3:15 pmSimpson Bay Princess Juliana
$649
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 August 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

Mon 9/15

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 9/22

5:05 am-2:00 pm

1 stop7h 55m

$342

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:18 am

2 stops20h 13m

Chicago O'Hare Intl

Mon 9/22

5:05 am-2:00 pm

1 stop7h 55m

$443

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 9/5

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Thu 9/11

5:17 pm-2:00 pm

3 stops19h 43m

$448

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 9/5

2:35 pm-6:23 pm

1 stop28h 48m

Chicago O'Hare Intl

Thu 9/11

1:35 pm-1:15 pm

1 stop22h 40m

$465

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 9/5

3:10 pm-12:28 pm

2 stops22h 18m

Chicago Midway

Thu 9/11

1:08 pm-1:50 pm

2 stops23h 42m

$603

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 9/15

2:20 pm-7:47 am

2 stops18h 27m

Chicago O'Hare Intl

Mon 9/22

9:37 pm-1:19 pm

2 stops14h 42m

$617

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:24 pm-7:25 am

2 stops16h 01m

Chicago O'Hare Intl

Wed 10/15

8:44 pm-1:37 pm

2 stops15h 53m

$621

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 9/5

3:10 pm-8:35 am

2 stops18h 25m

Chicago Midway

Thu 9/11

12:43 pm-1:50 pm

1 stop24h 07m

$807

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 9/5

11:35 am-5:37 pm

3 stops31h 02m

Chicago Midway

Thu 9/11

5:20 pm-10:50 am

2 stops16h 30m

$1,333

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 9/5

11:35 am-5:37 pm

3 stops31h 02m

Chicago Midway

Thu 9/11

9:20 am-10:50 am

3 stops24h 30m

$1,457

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 in the afternoon. Flights from Simpson Bay to Chicago during this time can be as low as $614. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $735.

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 33% 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

Best Price Found

$200

Fastest flight time

7h 44m

Direct flights

Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Simpson Bay in the past 72 hours is $200. The best round-trip flight deal from Simpson Bay to Chicago found on momondo in the last 72 hours is $342.
The fastest flight from Simpson Bay to Chicago takes 7h 44m
Direct flights go from Simpson Bay to Chicago on Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • 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 8h 34m.

  • 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 many operators does momondo search for flights from Simpson Bay Princess Juliana Airport to Chicago?

  • 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?

Best airlines flying from Simpson Bay to Chicago

Compare and see reviews for airlines that fly from Simpson Bay to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $554Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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