Question 1

How long does a flight from Simpson Bay to Chicago take?

Accepted Answer

Flying to Chicago from Simpson Bay requires at least one layover, as there are no direct flights for this route. The shortest flight duration is 5h 54m. Visit our flight page for the latest deals!>/a>

Question 2

What is the cheapest flight from Simpson Bay to Chicago?

Accepted Answer

In the last 3 days, the lowest price for a flight from Simpson Bay to Chicago was $199 for a one-way ticket and $329 for a round-trip. <a href='/flight-routes/Simpson-Bay-Princess-Juliana-SXM/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 3

Do I need a passport to fly between Simpson Bay and Chicago?

Accepted Answer

Yes, you'll most likely have to show a valid passport before boarding the plane in Simpson Bay and on arrival in Chicago. <a href='/flight-routes/Simpson-Bay-Princess-Juliana-SXM/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 4

What’s the cheapest day of the week to fly from Simpson Bay to Chicago?

Accepted Answer

If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Simpson Bay to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Saturdays for the best deals. Visit our flight page for the latest deals!>/a>

Question 5

What’s the cheapest day of the week to fly from Simpson Bay to Chicago?

Accepted Answer

If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Simpson Bay to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Saturdays for the best deals. Visit our flight page for the latest deals!>/a>

Question 6

Which airports will I be using when flying from Simpson Bay to Chicago?

Accepted Answer

When flying out of Simpson Bay you will be using Simpson Bay Princess Juliana. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl. <a href='/flight-routes/Simpson-Bay-Princess-Juliana-SXM/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 7

Which aircraft models fly most regularly from Simpson Bay to Chicago?

Accepted Answer

The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Simpson Bay to Chicago flight route.

Question 8

Which airline alliances offer flights from Simpson Bay to Chicago?

Accepted Answer

Star Alliance, oneworld, and SkyTeam are the airline alliances operating flights between Simpson Bay and Chicago, with Star Alliance being the most commonly used for this route.

Question 9

How does KAYAK find such low prices on flights from Simpson Bay 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 from Simpson Bay to Chicago. <a href='/flight-routes/Simpson-Bay-Princess-Juliana-SXM/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 10

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

Accepted Answer

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

Question 11

What is the Hacker Fare option on flights from Simpson Bay 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 to Simpson Bay with another airline. <a href='/flight-routes/Simpson-Bay-Princess-Juliana-SXM/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 12

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Simpson Bay 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 from Simpson Bay up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. <a href='/flight-routes/Simpson-Bay-Princess-Juliana-SXM/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 13

What is the cheapest layover airport when flying from Simpson Bay to Chicago?

Accepted Answer

Flights via Fort Lauderdale (FLL) offer the most affordable fares, with an average round-trip price of $405.

Question 14

What is the most popular layover airport when flying from Simpson Bay to Chicago?

Accepted Answer

Miami (MIA) is the top choice – 38% of KAYAK users who clicked on 1-stop flights from Simpson Bay to Chicago picked an itinerary connecting there.

Question 15

Which layover airport has the quickest connection when flying from Simpson Bay to Chicago?

Accepted Answer

If you prefer a quick connection, Miami (MIA) often has the shortest layovers from Simpson Bay to Chicago, with an average of 1h 38m.

Question 16

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

Accepted Answer

Consider flying via Charlotte (CLT) for the shortest journey. The average one-way travel time for flights connecting there is 8h 25m.

Question 17

Which cabin class options are there for flights between Simpson Bay and Chicago?

Accepted Answer

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 18

Which cabin class options are there for flights between Simpson Bay and Chicago?

Accepted Answer

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 19

Which airlines provide the cheapest flights from Simpson Bay to Chicago?

Accepted Answer

In the past 3 days, the cheapest round-trip tickets from Simpson Bay to Chicago were found on Spirit Airlines ($329) and Air Canada ($452).

Question 20

Which airlines provide the cheapest flights from Simpson Bay to Chicago?

Accepted Answer

In the past 3 days, the cheapest round-trip tickets from Simpson Bay to Chicago were found on Spirit Airlines ($329) and Air Canada ($452).

Question 21

What is the cheapest Simpson Bay to Chicago flight route?

Accepted Answer

The cheapest return flight from Simpson Bay to Chicago costs $389 on the route between Simpson Bay (SXM) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

Question 22

What is the cheapest Simpson Bay to Chicago flight route?

Accepted Answer

The cheapest return flight from Simpson Bay to Chicago costs $389 on the route between Simpson Bay (SXM) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

SXM - CHI

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KAYAK's insights & trends for Simpson Bay to Chicago flights

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

What is the cheapest Simpson Bay to Chicago flight route?

The cheapest return flight from Simpson Bay to Chicago costs $389 on the route between Simpson Bay (SXM) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Simpson Bay to Chicago?

Which airlines provide the cheapest flights from Simpson Bay to Chicago?

In the past 3 days, the cheapest round-trip tickets from Simpson Bay to Chicago were found on Spirit Airlines ($329) and Air Canada ($452).

What is the most popular layover airport when flying from Simpson Bay to Chicago?

Miami (MIA) is the top choice – 38% of KAYAK users who clicked on 1-stop flights from Simpson Bay to Chicago picked an itinerary connecting there.

What is the cheapest layover airport when flying from Simpson Bay to Chicago?

Flights via Fort Lauderdale (FLL) offer the most affordable fares, with an average round-trip price of $405.

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

Consider flying via Charlotte (CLT) for the shortest journey. The average one-way travel time for flights connecting there is 8h 25m.

Which layover airport has the quickest connection when flying from Simpson Bay to Chicago?

If you prefer a quick connection, Miami (MIA) often has the shortest layovers from Simpson Bay to Chicago, with an average of 1h 38m.

Which cabin class options are there for flights between Simpson Bay and Chicago?

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Simpson Bay to Chicago take?

Flying to Chicago from Simpson Bay requires at least one layover, as there are no direct flights for this route. The shortest flight duration is 5h 54m.

Good to know

When to book flights from Simpson Bay to Chicago

FAQs for booking flights from Simpson Bay to Chicago

What is the cheapest flight from Simpson Bay to Chicago?

In the last 3 days, the lowest price for a flight from Simpson Bay to Chicago was $199 for a one-way ticket and $329 for a round-trip.

Do I need a passport to fly between Simpson Bay and Chicago?

Yes, you'll most likely have to show a valid passport before boarding the plane in Simpson Bay and on arrival in Chicago.

Which airports will I be using when flying from Simpson Bay to Chicago?

When flying out of Simpson Bay you will be using Simpson Bay Princess Juliana. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

Which aircraft models fly most regularly from Simpson Bay to Chicago?

The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Simpson Bay to Chicago flight route.

Which airline alliances offer flights from Simpson Bay to Chicago?

Star Alliance, oneworld, and SkyTeam are the airline alliances operating flights between Simpson Bay and Chicago, with Star Alliance being the most commonly used for this route.

How does KAYAK find such low prices on flights from Simpson Bay 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 from Simpson Bay to Chicago.

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

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

What is the Hacker Fare option on flights from Simpson Bay 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 to Simpson Bay with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Simpson Bay 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 from Simpson Bay up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Simpson Bay to Chicago

Prefer to fly direct from Simpson Bay to Chicago?

Everything you need to know for your flight from Simpson Bay to Chicago

Information on your arrival and departure airports

Cabin class types available on flights from Simpson Bay to Chicago

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

Find direct flights to and from Simpson Bay and Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight