Question 1

How long is the flight to Chicago?

Accepted Answer

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Simpson Bay, which takes 5h 46m.

Question 2

How long is the flight to Chicago?

Accepted Answer

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Simpson Bay, which takes 5h 46m.

Question 3

What is the cheapest flight to Chicago?

Accepted Answer

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Simpson Bay, at $376 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $137 in the last 3 days. Visit our flight page for the latest deals!>/a>

Question 4

What is the cheapest flight to Chicago?

Accepted Answer

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Simpson Bay, at $376 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $137 in the last 3 days. Visit our flight page for the latest deals!>/a>

Question 5

Which Chicago airport is closest to central Chicago?

Accepted Answer

The distance between Chicago Midway Airport and downtown Chicago is 9 miles, which makes it the closest of the 3 Chicago airports. Chicago O'Hare Airport is 16 miles away from the center and Chicago Greater Rockford is 79 miles away. <a href='/flight-routes/Sint-Maarten-SX0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 6

How many cities have direct flights to Chicago?

Accepted Answer

From St. Maarten, there are direct flights to Chicago from 1 city. This city is Simpson Bay and there are 3 direct flights each week.

Question 7

How many cities have direct flights to Chicago?

Accepted Answer

From St. Maarten, there are direct flights to Chicago from 1 city. This city is Simpson Bay and there are 3 direct flights each week.

Question 8

Which is the cheapest airport to fly into in Chicago?

Accepted Answer

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $151.

Question 9

Which is the cheapest airport to fly into in Chicago?

Accepted Answer

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $151.

Question 10

How much is a flight to Chicago?

Accepted Answer

On average, a flight to Chicago costs $490. The cheapest price found on KAYAK in the last 2 weeks cost $347 and departed from Simpson Bay Princess Juliana Airport.

Question 11

What is the cheapest day to fly to Chicago?

Accepted Answer

Based on KAYAK data, the cheapest day to fly to Chicago is Monday where round-trip tickets can be as cheap as $372. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $610 on average.

Question 12

What is the cheapest day to fly to Chicago?

Accepted Answer

Based on KAYAK data, the cheapest day to fly to Chicago is Monday where round-trip tickets can be as cheap as $372. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $610 on average.

Question 13

How does KAYAK find such low prices on flights to Chicago?

Accepted Answer

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago. <a href='/flight-routes/Sint-Maarten-SX0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 14

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

Accepted Answer

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now. <a href='/flight-routes/Sint-Maarten-SX0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 15

What is the Hacker Fare option on flights to Chicago?

Accepted Answer

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline. <a href='/flight-routes/Sint-Maarten-SX0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 16

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

Accepted Answer

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. <a href='/flight-routes/Sint-Maarten-SX0/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 17

Which airline offers the most flights to Chicago?

Accepted Answer

Of the 2 airlines that fly to Chicago, United Airlines offers the most flights, with around 2 per week, followed by American Airlines with 1 flights per week.

Question 18

Which airline offers the most flights to Chicago?

Accepted Answer

Of the 2 airlines that fly to Chicago, United Airlines offers the most flights, with around 2 per week, followed by American Airlines with 1 flights per week.

Question 19

How many airports are there in Chicago?

Accepted Answer

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 94% of all flights arriving there.

Question 20

How many airports are there in Chicago?

Accepted Answer

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 94% of all flights arriving there.

Question 21

What is the cheapest time of day to fly to Chicago?

Accepted Answer

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $586 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $586.

Question 22

What is the cheapest time of day to fly to Chicago?

Accepted Answer

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $586 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $586.

Question 23

How many direct flights to Chicago are there each day?

Accepted Answer

There are around 2,450 direct flights from within St. Maarten to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 48% of flights departing in the morning.

Question 24

How many direct flights to Chicago are there each day?

Accepted Answer

There are around 2,450 direct flights from within St. Maarten to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 48% of flights departing in the morning.

Question 25

How many direct flights to Chicago are there each week?

Accepted Answer

Each week there are around 17,148 direct flights from within St. Maarten to Chicago. The most common day for departures is Monday, with 15% of flights taking off on this day.

Question 26

How many direct flights to Chicago are there each week?

Accepted Answer

Each week there are around 17,148 direct flights from within St. Maarten to Chicago. The most common day for departures is Monday, with 15% of flights taking off on this day.

Question 27

How many long-haul flights are there to Chicago each week?

Accepted Answer

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 3 medium-haul flights (3-6 hour flight duration), with the most arriving from Simpson Bay.

Question 28

How many long-haul flights are there to Chicago each week?

Accepted Answer

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 3 medium-haul flights (3-6 hour flight duration), with the most arriving from Simpson Bay.

$218 Find Cheap Flights from St. Maarten to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Cheap Flights from St. Maarten to Chicago

Recent round-trip flight deals from St. Maarten to Chicago

Recent one-way flight deals from St. Maarten to Chicago

Recent last minute flight deals from St. Maarten to Chicago

Recent direct flight deals from St. Maarten to Chicago

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Simpson Bay, at $376 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $137 in the last 3 days.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Monday where round-trip tickets can be as cheap as $372. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $610 on average.

What is the cheapest time of day to fly to Chicago?

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $586 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $586.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $151.

Which airline offers the most flights to Chicago?

Of the 2 airlines that fly to Chicago, United Airlines offers the most flights, with around 2 per week, followed by American Airlines with 1 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 94% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Simpson Bay, which takes 5h 46m.

How many direct flights to Chicago are there each day?

There are around 2,450 direct flights from within St. Maarten to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 48% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 17,148 direct flights from within St. Maarten to Chicago. The most common day for departures is Monday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 3 medium-haul flights (3-6 hour flight duration), with the most arriving from Simpson Bay.

How many cities have direct flights to Chicago?

From St. Maarten, there are direct flights to Chicago from 1 city. This city is Simpson Bay and there are 3 direct flights each week.

Good to know

FAQs - booking Chicago flights

What is the cheapest flight to Chicago?

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Simpson Bay, at $376 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $137 in the last 3 days.

Which Chicago airport is closest to central Chicago?

The distance between Chicago Midway Airport and downtown Chicago is 9 miles, which makes it the closest of the 3 Chicago airports. Chicago O'Hare Airport is 16 miles away from the center and Chicago Greater Rockford is 79 miles away.

How much is a flight to Chicago?

On average, a flight to Chicago costs $490. The cheapest price found on KAYAK in the last 2 weeks cost $347 and departed from Simpson Bay Princess Juliana Airport.

How does KAYAK find such low prices on flights to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from local origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight