Which airport is the most popular layover for flights between Chicago and Simpson Bay?

Fort Lauderdale (FLL) was the most common stop: 39% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Simpson Bay?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $431.

What airlines fly to Simpson Bay?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Simpson Bay from Chicago according to our data. American Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 4 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Simpson Bay Princess Juliana?

Spirit Airlines, Air Canada, and United Airlines are the most popular carriers operating from Chicago to Simpson Bay Princess Juliana

Which layover airport has the shortest travel time from Chicago to Simpson Bay?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 6h 41m.

Which layover airport has the shortest connection time from Chicago to Simpson Bay?

Charlotte (CLT) has the shortest average layover time for this route: 1h 11m.

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

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

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

As of August 2025, there are 4 operators available to choose from for flights from Chicago to Simpson Bay Princess Juliana Airport.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The required travel and health documents for your Simpson Bay Princess Juliana Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$139 Cheap Flights from Chicago to Simpson Bay (CHI-SXM) in 2025

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Simpson Bay (CHI-SXM)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:05 am - 2:00 pmORD-SXM

7h 55m1 stop

3:05 pm - 10:48 pmSXM-ORD

8h 43m1 stop

$337Spirit Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

5:05 am - 1:59 pmORD-SXM

7h 54m1 stop

3:05 pm - 1:03 amSXM-ORD

10h 58m1 stop

$341Spirit Airlines

Find Deal

Sat, Oct 18 - Sat, Nov 1

5:05 am - 3:10 pmORD-SXM

8h 05m1 stop

4:28 pm - 11:42 pmSXM-ORD

9h 14m1 stop

$347Spirit Airlines

Find Deal

Mon, Nov 10 - Sat, Nov 15

7:41 pm - 7:30 pmORD-SXM

22h 49m3 stops

3:05 pm - 12:33 pmSXM-ORD

22h 28m2 stops

$521

Find Deal

Sat, Oct 18 - Sat, Nov 1

3:55 pm - 2:40 pmORD-SXM

20h 45m2 stops

4:28 pm - 11:42 pmSXM-ORD

9h 14m1 stop

$528

Find Deal

Sat, Jan 17 - Sat, Jan 24

3:35 pm - 4:00 pmORD-SXM

22h 25m2 stops

5:00 pm - 11:18 amSXM-ORD

20h 18m2 stops

$557Air Canada

Find Deal

Thu, Dec 11 - Mon, Dec 15

6:45 am - 1:15 pmORD-SXM

29h 30m1 stop

2:35 pm - 12:10 pmSXM-ORD

22h 35m1 stop

$565JetBlue

Find Deal

Mon, Oct 6 - Wed, Oct 15

3:35 pm - 4:00 pmORD-SXM

22h 25m2 stops

5:00 pm - 11:06 amSXM-ORD

20h 06m2 stops

$566Air Canada

Find Deal

Fri, Jan 16 - Fri, Jan 23

6:00 am - 1:50 pmMDW-SXM

6h 50m1 stop

3:20 pm - 8:40 amSXM-MDW

18h 20m2 stops

$747Delta

Find Deal

Sat, Sep 27 - Fri, Oct 3

6:00 am - 1:50 pmMDW-SXM

6h 50m1 stop

3:20 pm - 8:40 amSXM-MDW

18h 20m2 stops

$772Delta

Find Deal

Sat, Sep 27 - Sat, Oct 4

Spirit Airlines flights from Chicago to Simpson Bay

Our best Spirit Airlines deals on Chicago to Simpson Bay flight tickets

Spirit Airlines

Sep 27

ORD5:05 amChicago O'Hare Intl

7h 55m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Oct 4

SXM3:05 pmSimpson Bay Princess Juliana

8h 43m

1 stop

ORD10:48 pmChicago O'Hare Intl

$337

Find similar

Spirit Airlines

Oct 18

ORD5:05 amChicago O'Hare Intl

7h 54m

1 stop

SXM1:59 pmSimpson Bay Princess Juliana

Nov 1

SXM3:05 pmSimpson Bay Princess Juliana

10h 58m

1 stop

ORD1:03 amChicago O'Hare Intl

$341

Find similar

Spirit Airlines

Nov 10

ORD5:05 amChicago O'Hare Intl

8h 05m

1 stop

SXM3:10 pmSimpson Bay Princess Juliana

Nov 15

SXM4:28 pmSimpson Bay Princess Juliana

9h 14m

1 stop

ORD11:42 pmChicago O'Hare Intl

$347

Find similar

Delta flights from Chicago to Simpson Bay

Our best Delta deals on Chicago to Simpson Bay flight tickets

Delta

Sep 27

MDW6:00 amChicago Midway

6h 50m

1 stop

SXM1:50 pmSimpson Bay Princess Juliana

Oct 3

SXM3:20 pmSimpson Bay Princess Juliana

18h 20m

2 stops

MDW8:40 amChicago Midway

$747

Find similar

Delta

Sep 27

MDW6:00 amChicago Midway

6h 50m

1 stop

SXM1:50 pmSimpson Bay Princess Juliana

Oct 4

SXM3:20 pmSimpson Bay Princess Juliana

18h 20m

2 stops

MDW8:40 amChicago Midway

$772

Find similar

Delta

Oct 18

MDW6:00 amChicago Midway

6h 49m

1 stop

SXM1:49 pmSimpson Bay Princess Juliana

Oct 25

SXM3:14 pmSimpson Bay Princess Juliana

8h 00m

1 stop

MDW10:14 pmChicago Midway

$807

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/27

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 11/1

3:05 pm-1:03 am

1 stop10h 58m

$341

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 11/10

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 11/15

4:28 pm-11:42 pm

1 stop9h 14m

$347

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

7:41 pm-7:30 pm

3 stops22h 49m

Simpson Bay Princess Juliana

Sat 11/1

3:05 pm-12:33 pm

2 stops22h 28m

$521

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/17

3:55 pm-2:40 pm

2 stops20h 45m

Simpson Bay Princess Juliana

Sat 1/24

4:28 pm-11:42 pm

1 stop9h 14m

$528

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

3:35 pm-4:00 pm

2 stops22h 25m

Simpson Bay Princess Juliana

Mon 12/15

5:00 pm-11:18 am

2 stops20h 18m

$557

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 10/6

6:45 am-1:15 pm

1 stop29h 30m

Simpson Bay Princess Juliana

Wed 10/15

2:35 pm-12:10 pm

1 stop22h 35m

$565

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/16

3:35 pm-4:00 pm

2 stops22h 25m

Simpson Bay Princess Juliana

Fri 1/23

5:00 pm-11:06 am

2 stops20h 06m

$566

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 9/27

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 10/3

3:20 pm-8:40 am

2 stops18h 20m

$747

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 9/27

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 10/4

3:20 pm-8:40 am

2 stops18h 20m

$772

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Simpson Bay

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

Prices

Airlines

Layovers

What is the cheapest month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Chicago to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $642. If you aren’t able to travel to Simpson Bay during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $654.

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $644. Flights from Chicago to Simpson Bay on a Saturday will generally be more expensive and average around $903. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

According to our data, the cheapest time of day to fly to Simpson Bay is at noon. momondo users have found flights departing from Chicago to Simpson Bay at noon for as low as $417. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $886.

What is the cheapest Chicago to Simpson Bay Princess Juliana flight route?

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

How far in advance should I book a flight to Simpson Bay?

You are more likely to see cheaper flights to Simpson Bay from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $702 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Chicago for as low as $549 on momondo.

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

There are 2 cabin classes available to choose from on Chicago to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Chicago to Simpson Bay

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

Estimated round-trip price

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

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

Best Price Found	$368
Fastest flight time	4h 45m
Direct flights	Mon and Sun
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Chicago in the past 72 hours is $368. The best round-trip flight deal from Chicago to Simpson Bay found on momondo in the last 72 hours is $797.

The fastest flight from Chicago to Simpson Bay takes 4h 45m

Direct flights go from Chicago to Simpson Bay on Monday and Sunday. There are no airlines offering direct flights.

There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

Search flight deals

How far is Chicago to Simpson Bay Princess Juliana by plane?
A flight from Chicago to Simpson Bay Princess Juliana will travel around 2188.1 mi. Typically, this will take 6h 49m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Simpson Bay Princess Juliana Airport?
Prices for flights from Chicago to Simpson Bay Princess Juliana Airport were last updated today.
How many operators does momondo search for flights from Chicago to Simpson Bay Princess Juliana Airport?
As of August 2025, there are 4 operators available to choose from for flights from Chicago to Simpson Bay Princess Juliana Airport.
How old do you have to be to fly from Chicago to Simpson Bay Princess Juliana Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The required travel and health documents for your Simpson Bay Princess Juliana Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Simpson Bay?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Simpson Bay is Boeing 737-700, representing 45.56% of all bookings. The subsequent popular models are Airbus A319 at 38.89% and Boeing 737 MAX 8 at 15.56%.
What is the most popular airline from Chicago to Simpson Bay?
momondo data reveals that the most frequently booked airline on the route from Chicago to Simpson Bay is American Airlines, representing 51% of all bookings. The subsequent popular airlines are United Airlines at 20%, Spirit Airlines at 15%, and Delta at 14%.

Best airlines flying from Chicago to Simpson Bay

Compare and see reviews for airlines that fly from Chicago to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $316	Free Cancellation	Rating 6.3 8,029 reviews	Search Spirit Airlines flights
Delta	PriceFrom $564	Free Cancellation	Rating 7.9 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $616	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $654	Free Cancellation	Rating 7.4 8,940 reviews	Search United Airlines flights

Philipsburg

Why use momondo?

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

It is quick and easy to find Chicago to Simpson Bay 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 Simpson Bay that suits you.

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

Yes. momondo allows you to filter the results for Chicago to Simpson Bay flights to just show those with flexible booking policies.

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

Once you have performed a search for Chicago to Simpson Bay flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Chicago to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sat 8/30

Sat 9/6

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Cheap flights from Chicago to Simpson Bay from $139

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Simpson Bay departing on 9/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Simpson Bay (CHI-SXM)

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Chicago to Simpson Bay

Our best Spirit Airlines deals on Chicago to Simpson Bay flight tickets

Delta flights from Chicago to Simpson Bay

Our best Delta deals on Chicago to Simpson Bay flight tickets

momondo Fare Finder

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

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Chicago to Simpson Bay

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 month to fly to Simpson Bay?

What is the cheapest day to depart on your flight to Simpson Bay?

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

What is the cheapest Chicago to Simpson Bay Princess Juliana flight route?

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

How far in advance should I book a flight to Simpson Bay?

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

There are 2 cabin classes available to choose from on Chicago to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest airline that flies from Chicago to Simpson Bay Princess Juliana?

Spirit Airlines, Air Canada, and United Airlines are the most popular carriers operating from Chicago to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

Which airport is the most popular layover for flights between Chicago and Simpson Bay?

Fort Lauderdale (FLL) was the most common stop: 39% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Simpson Bay?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $431.

Which layover airport has the shortest travel time from Chicago to Simpson Bay?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 6h 41m.

Which layover airport has the shortest connection time from Chicago to Simpson Bay?

Charlotte (CLT) has the shortest average layover time for this route: 1h 11m.

When to book flights from Chicago to Simpson Bay

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Simpson Bay

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

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

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

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

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

What is the most popular plane model from Chicago to Simpson Bay?

What is the most popular airline from Chicago to Simpson Bay?

Best airlines flying from Chicago to Simpson Bay

Compare and see reviews for airlines that fly from Chicago to Simpson Bay with momondo

Traveling to a place near Simpson Bay?

Why use momondo?

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

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

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

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

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo