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 10h 17m.

Question 2

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 3

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 $119.

Question 4

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 Sunday, where round-trip prices are $773 on average.

Question 5

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 6

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 7

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 8

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 9

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 evening, when round-trip flights cost $614 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 $735.

Question 10

How many direct flights to Chicago are there each day?

Accepted Answer

There are around 1,599 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 49% of flights departing in the morning.

Question 11

How many direct flights to Chicago are there each week?

Accepted Answer

Each week there are around 11,193 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.

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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 $119.

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 10h 17m.

How many direct flights to Chicago are there each day?

There are around 1,599 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 49% of flights departing in the morning.

Good to know

FAQs - booking Chicago flights

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.

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 Sunday, where round-trip prices are $773 on average.

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.

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

The cheapest time of day to fly to Chicago is generally in the evening, when round-trip flights cost $614 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 $735.

How many direct flights to Chicago are there each week?

Each week there are around 11,193 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.

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