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 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.

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

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

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

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $445.

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

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 25% 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: 28% 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 52% 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.

How often are flights from Chicago to Simpson Bay delayed?

Historically, on average around 35% 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 97 minutes.

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 January 2026, 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.

$75 Cheap Flights from Chicago to Simpson Bay in 2026

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Round-trip

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:15 am - 2:15 pm

ORD

SXM

7h 00m

1 stop

3:20 pm - 11:47 pm

SXM

ORD

10h 27m

1 stop

$219Spirit Airlines

Mon, Feb 9 - Wed, Feb 18

5:15 am - 2:15 pm

ORD

SXM

7h 00m

1 stop

3:20 pm - 11:47 pm

SXM

ORD

10h 27m

1 stop

$227Spirit Airlines

Wed, Feb 18 - Wed, Feb 25

5:15 am - 2:15 pm

ORD

SXM

7h 00m

1 stop

3:20 pm - 11:47 pm

SXM

ORD

10h 27m

1 stop

$235Spirit Airlines

Sat, Feb 7 - Sat, Feb 14

5:15 am - 2:15 pm

ORD

SXM

7h 00m

1 stop

3:20 pm - 11:47 pm

SXM

ORD

10h 27m

1 stop

$245Spirit Airlines

Mon, Feb 9 - Wed, Feb 18

8:16 pm - 2:15 pm

ORD

SXM

15h 59m

1 stop

3:20 pm - 10:39 pm

SXM

ORD

9h 19m

1 stop

$250Multiple Airlines

Mon, Feb 23 - Sat, Feb 28

5:30 am - 2:20 pm

ORD

SXM

7h 50m

1 stop

2:11 pm - 11:41 pm

SXM

ORD

10h 30m

1 stop

$269Multiple Airlines

Sat, Apr 11 - Wed, Apr 15

6:00 am - 3:20 pm

MDW

SXM

7h 20m

1 stop

3:41 pm - 11:20 pm

SXM

MDW

8h 39m

1 stop

$426Frontier

Sat, Mar 7 - Sat, Mar 14

6:00 am - 2:20 pm

MDW

SXM

7h 20m

1 stop

3:25 pm - 8:07 pm

SXM

MDW

29h 42m

1 stop

$482Frontier

Sat, Apr 4 - Sat, Apr 11

6:00 am - 2:50 pm

MDW

SXM

6h 50m

1 stop

1:38 pm - 10:31 pm

SXM

MDW

10h 53m

1 stop

$529Delta

Wed, Feb 18 - Wed, Feb 25

6:00 am - 2:50 pm

MDW

SXM

6h 50m

1 stop

1:38 pm - 10:31 pm

SXM

MDW

10h 53m

1 stop

$559Delta

Sat, Feb 21 - Wed, Feb 25

Spirit Airlines flights from Chicago to Simpson Bay

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

Spirit Airlines

Feb 9

ORD5:15 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:15 pmSimpson Bay Princess Juliana

Feb 18

SXM3:20 pmSimpson Bay Princess Juliana

10h 27m

1 stop

ORD11:47 pmChicago O'Hare Intl

$219

Spirit Airlines

Feb 18

ORD5:15 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:15 pmSimpson Bay Princess Juliana

Feb 25

SXM3:20 pmSimpson Bay Princess Juliana

10h 27m

1 stop

ORD11:47 pmChicago O'Hare Intl

$227

Spirit Airlines

Feb 7

ORD5:15 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:15 pmSimpson Bay Princess Juliana

Feb 14

SXM3:20 pmSimpson Bay Princess Juliana

10h 27m

1 stop

ORD11:47 pmChicago O'Hare Intl

$235

Delta flights from Chicago to Simpson Bay

Our best Delta deals on Chicago to Simpson Bay flight tickets

Delta

Feb 18

MDW6:00 amChicago Midway

6h 50m

1 stop

SXM2:50 pmSimpson Bay Princess Juliana

Feb 25

SXM1:38 pmSimpson Bay Princess Juliana

10h 53m

1 stop

MDW10:31 pmChicago Midway

$529

Delta

Feb 21

MDW6:00 amChicago Midway

6h 50m

1 stop

SXM2:50 pmSimpson Bay Princess Juliana

Feb 25

SXM1:38 pmSimpson Bay Princess Juliana

10h 53m

1 stop

MDW10:31 pmChicago Midway

$559

Delta

Mar 2

MDW6:00 amChicago Midway

6h 50m

1 stop

SXM2:50 pmSimpson Bay Princess Juliana

Mar 5

SXM1:38 pmSimpson Bay Princess Juliana

10h 53m

1 stop

MDW10:31 pmChicago Midway

$573

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/9

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Wed 2/18

3:20 pm-11:47 pm

1 stop10h 27m

$219

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 2/18

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Wed 2/25

3:20 pm-11:47 pm

1 stop10h 27m

$227

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 2/14

3:20 pm-11:47 pm

1 stop10h 27m

$235

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/9

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Wed 2/18

3:20 pm-11:47 pm

1 stop10h 27m

$245

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/23

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Sat 2/28

3:20 pm-10:39 pm

1 stop9h 19m

$250

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/11

5:30 am-2:20 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Wed 4/15

2:11 pm-11:41 pm

1 stop10h 30m

$269

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 3/7

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 3/14

3:41 pm-11:20 pm

1 stop8h 39m

$426

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/4

6:00 am-2:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 4/11

3:25 pm-8:07 pm

1 stop29h 42m

$482

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 2/18

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Wed 2/25

1:38 pm-10:31 pm

1 stop10h 53m

$529

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Wed 2/25

1:38 pm-10:31 pm

1 stop10h 53m

$559

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

Delays

Layovers

What is the typical price of a round-trip flight between Chicago and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

In general, January 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 $586. If you aren’t able to travel to Simpson Bay during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $600.

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

Our data shows that Sunday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $737. Flights from Chicago to Simpson Bay on a Saturday will generally be more expensive and average around $822. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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 $659 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 $495 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 65% 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	$677
Fastest flight time	5h 03m
Direct flights	Mon and Sun
Airports in Simpson Bay	1 airport

The best flight deal from Chicago to Simpson Bay found on momondo in the last 72 hours is $677

The fastest flight from Chicago to Simpson Bay takes 5h 03m

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

There is 1 airport in Simpson Bay. From Chicago there are direct flights to 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 5h 03m 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 January 2026, 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 60.19% of all bookings. The subsequent popular models are Airbus A319 at 23.30%, Boeing 737-700 at 5.83%, and Airbus A320-100/200 at 4.85%.
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 55% of all bookings. The subsequent popular airlines are United Airlines at 18%, Spirit Airlines at 16%, and Delta at 11%.

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 $280	Free Cancellation	Rating 6.3 8,364 reviews	Search Spirit Airlines flights
Delta	PriceFrom $290	Free Cancellation	Rating 7.9 8,089 reviews	Search Delta flights
United Airlines	PriceFrom $410	Free Cancellation	Rating 7.4 9,191 reviews	Search United Airlines flights
American Airlines	PriceFrom $501	Free Cancellation	Rating 7.2 11,174 reviews	Search American Airlines flights
JetBlue	PriceFrom $535	Free Cancellation	Rating 7.2 2,890 reviews	Search JetBlue 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.

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Fly your favorite airline to Simpson Bay

Cheap flights from Chicago to Simpson Bay from $84

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 2/18. 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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Spirit Airlines flights from Chicago to Simpson Bay

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

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See travel insights to Simpson Bay from

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

What is the typical price of a round-trip flight between Chicago and Simpson Bay?

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 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 65% 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 and Frontier 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 35% 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 97 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, American Airlines have had the least number of delays on this route over the last 12 months; with about 25% 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: 28% 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 $445.

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.

Find better results for your trip to St. Maarten