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

Spirit Airlines, Frontier, and Delta are the most popular carriers operating from Chicago to Simpson Bay Princess Juliana

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

Fort Lauderdale (FLL) was the most common stop: 35% of momondo users choosing 1-stop flights on this route connected there.

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 53% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

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 44m.

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.

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 $399.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How often are flights from Chicago to Simpson Bay delayed?

Historically, on average around 37% of flights between Chicago and Simpson Bay have experienced a delay on any given week. The average delay length over the past 12 months has been 129 minutes.

What is the most punctual flight time for Chicago to Simpson Bay flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Which airline has the best punctuality record on Chicago to Simpson Bay flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 36% of their flights experiencing any sort of delay.

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 December 2025, there are 5 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.

$78 Cheap Flights from Chicago to Simpson Bay in 2025/26

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5:15 am - 2:10 pm

ORD

SXM

6h 55m1 stop

3:15 pm - 10:03 pm

SXM

ORD

8h 48m1 stop

$232Spirit Airlines

Sat, Jan 24 - Sat, Jan 31

5:15 am - 2:10 pm

ORD

SXM

6h 55m1 stop

3:15 pm - 10:03 pm

SXM

ORD

8h 48m1 stop

$233Spirit Airlines

Sat, Jan 24 - Sat, Jan 31

8:43 pm - 2:10 pm

ORD

SXM

15h 27m1 stop

3:15 pm - 10:03 pm

SXM

ORD

8h 48m1 stop

$237Spirit Airlines

Thu, Jan 22 - Sat, Jan 31

5:15 am - 2:10 pm

ORD

SXM

6h 55m1 stop

3:15 pm - 10:03 pm

SXM

ORD

8h 48m1 stop

$239Spirit Airlines

Sat, Jan 24 - Sat, Jan 31

5:15 am - 2:10 pm

ORD

SXM

6h 55m1 stop

3:15 pm - 12:18 am

SXM

ORD

11h 03m1 stop

$240Spirit Airlines

Tue, Feb 17 - Sat, Feb 21

6:00 am - 3:20 pm

MDW

SXM

7h 20m1 stop

4:30 pm - 11:25 pm

SXM

MDW

8h 55m1 stop

$281Frontier

Sat, Feb 21 - Sat, Feb 28

6:00 am - 3:20 pm

MDW

SXM

7h 20m1 stop

4:30 pm - 11:25 pm

SXM

MDW

8h 55m1 stop

$287Frontier

Sat, Feb 21 - Sat, Feb 28

6:00 am - 3:20 pm

MDW

SXM

7h 20m1 stop

4:30 pm - 11:25 pm

SXM

MDW

8h 55m1 stop

$308Frontier

Sat, Feb 21 - Sat, Feb 28

6:00 am - 2:55 pm

MDW

SXM

6h 55m1 stop

1:55 pm - 10:22 pm

SXM

MDW

10h 27m1 stop

$355Delta

Sun, Jan 25 - Thu, Jan 29

9:32 am - 12:30 pm

MDW

SXM

24h 58m2 stops

1:55 pm - 10:22 pm

SXM

MDW

10h 27m1 stop

$360Delta

Sun, Jan 25 - Thu, Jan 29

Frontier flights from Chicago to Simpson Bay

Our best Frontier deals on Chicago to Simpson Bay flight tickets

Frontier

Feb 21

MDW6:00 amChicago Midway

7h 20m

1 stop

SXM3:20 pmSimpson Bay Princess Juliana

Feb 28

SXM4:30 pmSimpson Bay Princess Juliana

8h 55m

1 stop

MDW11:25 pmChicago Midway

$281

Find similar

Frontier

Feb 21

MDW6:00 amChicago Midway

7h 20m

1 stop

SXM3:20 pmSimpson Bay Princess Juliana

Feb 28

SXM4:30 pmSimpson Bay Princess Juliana

8h 55m

1 stop

MDW11:25 pmChicago Midway

$287

Find similar

Frontier

Feb 21

MDW6:00 amChicago Midway

7h 20m

1 stop

SXM3:20 pmSimpson Bay Princess Juliana

Feb 28

SXM4:30 pmSimpson Bay Princess Juliana

8h 55m

1 stop

MDW11:25 pmChicago Midway

$308

Find similar

Spirit Airlines flights from Chicago to Simpson Bay

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

Spirit Airlines

Jan 24

ORD5:15 amChicago O'Hare Intl

6h 55m

1 stop

SXM2:10 pmSimpson Bay Princess Juliana

Jan 31

SXM3:15 pmSimpson Bay Princess Juliana

8h 48m

1 stop

ORD10:03 pmChicago O'Hare Intl

$232

Find similar

Spirit Airlines

Jan 24

ORD5:15 amChicago O'Hare Intl

6h 55m

1 stop

SXM2:10 pmSimpson Bay Princess Juliana

Jan 31

SXM3:15 pmSimpson Bay Princess Juliana

8h 48m

1 stop

ORD10:03 pmChicago O'Hare Intl

$233

Find similar

Spirit Airlines

Jan 22

ORD8:43 pmChicago O'Hare Intl

15h 27m

1 stop

SXM2:10 pmSimpson Bay Princess Juliana

Jan 31

SXM3:15 pmSimpson Bay Princess Juliana

8h 48m

1 stop

ORD10:03 pmChicago O'Hare Intl

$237

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-10:03 pm

1 stop8h 48m

$232

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-10:03 pm

1 stop8h 48m

$233

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/22

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-10:03 pm

1 stop8h 48m

$237

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-10:03 pm

1 stop8h 48m

$239

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 2/17

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 2/21

3:15 pm-12:18 am

1 stop11h 03m

$240

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$281

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$287

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$308

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 1/29

1:55 pm-10:22 pm

1 stop10h 27m

$355

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

9:32 am-12:30 pm

2 stops24h 58m

Simpson Bay Princess Juliana

Thu 1/29

1:55 pm-10:22 pm

1 stop10h 27m

$360

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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

Delays

Layovers

Other information

What is the cheapest month to fly to Simpson Bay?

In general, August 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 $585. If you aren’t able to travel to Simpson Bay during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $612.

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 $888. 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 $868.

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 $693 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 $524 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.

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

You could potentially save up to 25% on your flight if you consider stops on a Chicago to Simpson Bay flight.

How have Chicago to Simpson Bay flight prices changed over time?

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	$313
Fastest flight time	5h 12m
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 $313. The best round-trip flight deal from Chicago to Simpson Bay found on momondo in the last 72 hours is $542.

The fastest flight from Chicago to Simpson Bay takes 5h 12m

Direct flights go from Chicago to Simpson Bay on Monday and Sunday. The only airline offering direct flights is United Airlines.

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 50m 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 December 2025, there are 5 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 MAX 8, representing 50.86% of all bookings. The subsequent popular models are Airbus A319 at 29.31%, Boeing 737-700 at 10.34%, and Airbus A320-100/200 at 4.31%.
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 19%, Spirit Airlines at 15%, and Delta at 12%.

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 $315	Free Cancellation	Rating 6.3 8,157 reviews	Search Spirit Airlines flights
Delta	PriceFrom $318	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
United Airlines	PriceFrom $420	Free Cancellation	Rating 7.4 9,066 reviews	Search United Airlines flights
JetBlue	PriceFrom $535	Free Cancellation	Rating 7.2 2,899 reviews	Search JetBlue flights
American Airlines	PriceFrom $551	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights

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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

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Cheap flights from Chicago to Simpson Bay from $78

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 2/7. 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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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.

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

You could potentially save up to 25% on your flight if you consider stops on a Chicago to Simpson Bay flight.

How have Chicago to Simpson Bay flight prices changed over time?

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

Spirit Airlines, Frontier, and Delta are the most popular carriers operating from Chicago to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

How often are flights from Chicago to Simpson Bay delayed?

Historically, on average around 37% of flights between Chicago and Simpson Bay have experienced a delay on any given week. The average delay length over the past 12 months has been 129 minutes.

What is the most punctual flight time for Chicago to Simpson Bay flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Simpson Bay flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 36% of their flights experiencing any sort of delay.

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

Fort Lauderdale (FLL) was the most common stop: 35% 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 $399.

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 44m.

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.