CHI - SXM

$149 Find Cheap Flights from Chicago to Simpson Bay - Compare and Save

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Everything you should know

Cheapest round-trip
$364
Typical prices: $517-$797
Air Canada
Sun 11/11Mon 11/19
ORD - SXM • 1 stop
Cheapest non-stop
$658
Typical prices: $612-$950
American Airlines
Tue 1/2Tue 1/9
ORD - SXM • Non-stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Simpson Bay. You'll need to take a connecting flight to reach the destination.
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Top routes
MDW - SXM
Cheapest
ORD - SXM
Most popular
Insights
Insights
Avoid delays
American Airlines
Most punctual • 82% on-time
Morning
Best time • Fewest delays
Insights
Insights
When to book
8 weeks
in advance
Our data shows that travelers who book at least 8 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 28% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $405 (round-trip)
Charlotte Douglas (CLT)
Shortest trip • 7h 38m (one-way)
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Insights
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Flight Deals

Cheap Flights from Chicago to Simpson Bay (CHI-SXM)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Simpson Bay

Wed, Nov 11 - Thu, Nov 19
Air Canada Logo
1:55 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:45 pm - 1:11 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
23h 26m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Island
$364Air Canada
Sat, Oct 24 - Sat, Oct 31
Air Canada Logo
8:40 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
17h 05m1 stop Toronto Pearson Intl
Air Canada Logo
2:40 pm - 12:07 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
22h 27m1 stop Montreal Pierre Elliott Trudeau Intl
$364Air Canada
Fri, Nov 27 - Wed, Dec 2
Multiple Airlines Logo
1:55 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
2:30 pm - 11:28 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
10h 58m1 stop Fort Lauderdale
$406Multiple Airlines
Fri, Nov 27 - Wed, Dec 2
Multiple Airlines Logo
7:25 am - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
29h 20m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
2:30 pm - 11:28 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
10h 58m1 stop Fort Lauderdale
$406Multiple Airlines
Sun, Sep 13 - Sat, Sep 19
JetBlue Logo
6:00 am - 2:00 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
7h 00m1 stop Fort Lauderdale
JetBlue Logo
3:05 pm - 11:08 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 03m1 stop Fort Lauderdale
$427JetBlue
Sun, Sep 13 - Thu, Sep 17
JetBlue Logo
6:00 am - 2:00 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
7h 00m1 stop Fort Lauderdale
JetBlue Logo
3:05 pm - 11:08 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 03m1 stop Fort Lauderdale
$442JetBlue
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
6:49 pm - 2:30 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
17h 41m1 stop Charlotte Douglas
American Airlines Logo
4:25 pm - 8:15 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
5h 50mnonstop
$655American Airlines
Thu, Nov 26 - Sat, Dec 19
American Airlines Logo
7:50 pm - 2:25 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 35m1 stop Miami
American Airlines Logo
4:28 pm - 8:18 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
5h 50mnonstop
$655American Airlines
Sat, Nov 14 - Sat, Nov 21
United Airlines Logo
8:40 am - 3:57 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
5h 17mnonstop
United Airlines Logo
5:00 pm - 7:30 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
16h 30m1 stop Washington, D.C. Dulles Intl
$661United Airlines
Sat, Nov 14 - Sat, Nov 21
United Airlines Logo
8:40 am - 3:57 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
5h 17mnonstop
United Airlines Logo
5:00 pm - 7:30 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
16h 30m1 stop Washington, D.C. Dulles Intl
$661United Airlines
Booking Insights

Price, demand and travel trends for Chicago to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago to Simpson Bay with more confidence.

How much is a round-trip flight from Chicago to Simpson Bay?

Round-trip flights from Chicago to Simpson Bay start at $364. Prices are below average for this route right now, with typical round-trip fares ranging from $517 to $797. The lowest price found in the past 5 days was $364 on Air Canada.

What is the cheapest Chicago to Simpson Bay flight route?

There's little price difference between Chicago to Simpson Bay routes. They average around $666 round-trip, based on KAYAK data over the past 12 months.

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

Monday is the cheapest day of the week to fly from Chicago to Simpson Bay, it is 24% cheaper than the average day. Saturday is the most expensive day with flight prices 6% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago to Simpson Bay?

  • February is the cheapest month to fly from Chicago to Simpson Bay at $482 round-trip.
  • December ($791) and June ($790) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 64% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago to Simpson Bay the cheapest?

Flights from Chicago to Simpson Bay are cheapest 8 weeks before departure. Booking in this window typically costs about 37% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Chicago to Simpson Bay flights

Low season

August

Cheapest flight

$149
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 28% lower on average.
Flight from Chicago O'Hare Intl Airport to Simpson Bay

When to book flights from Chicago to Simpson Bay

Are your dates flexible? Find out the best times to travel from Chicago to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago to Simpson Bay flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Chicago to Simpson Bay flights?

    Among airlines operating Chicago to Simpson Bay flights:

    • American Airlines: offers extra legroom; offers free seat selection
    • United Airlines: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago to Simpson Bay?

    Only United Airlines operates flights between Chicago and Simpson Bay.

  • Which airports can I use when flying from Chicago to Simpson Bay?

    Flights from Chicago to Simpson Bay may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Simpson Bay Princess Juliana (SXM).

  • Which airlines include bags at no extra cost on Chicago to Simpson Bay flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • American Airlines: a cabin bag and a checked bag in Economy Class
    • United Airlines: a cabin bag and a checked bag in Business Class
    • Air Canada: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago to Simpson Bay?

    Only Economy Class is available on flights from Chicago to Simpson Bay.

  • How much can I save by taking a layover when flying from Chicago to Simpson Bay?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $405 round-trip via Fort Lauderdale (FLL), compared to $795 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago to Simpson Bay?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Chicago to Simpson Bay pass through?

    One-stop flights from Chicago to Simpson Bay most commonly connect through:

    • Fort Lauderdale (FLL) - 33% of one-stop connections
    • Miami (MIA) - 32% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 14% of one-stop connections
    • Charlotte Douglas (CLT) - 10% of one-stop connections

    Fort Lauderdale (FLL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago to Simpson Bay?

    Yes. Being flexible with your travel dates can save you up to 29% on the Chicago to Simpson Bay route. Monday is the cheapest departure day at $509 round-trip on average, while Saturday is the most expensive at $713, a difference of $204. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • At what point is a flight considered delayed from Chicago to Simpson Bay?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Simpson Bay route, 25% of flights were delayed in the past 3 months, with delays averaging 1 hour 57 minutes.

  • How long is a flight from Chicago to Simpson Bay?

    A nonstop flight from Chicago to Simpson Bay takes 5h 17m, covering 2,188 miles.

  • What are the earliest and latest flights from Chicago to Simpson Bay?

    These are the earliest and latest flight times available from Chicago to Simpson Bay:

    • Earliest: departs at 8:40 am and lands at 1:57 pm
    • Latest: departs at 8:40 am and lands at 1:57 pm.

    The flight takes about 5h 17m.

  • How expensive are last-minute Chicago to Simpson Bay flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 19% above the route average of $667. Book 8 weeks before departure for the lowest fares.

  • Do I need a passport to fly from Chicago to Simpson Bay?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How are flight prices from Chicago to Simpson Bay looking right now?

    One-way fares from Chicago to Simpson Bay are currently lower than usual. Average one-way flight prices are about $244, which is 25% below the typical average for this route.

  • How do delay rates compare for morning and evening flights from Chicago to Simpson Bay?

    Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • How much time can I save by choosing a different layover airport from Chicago to Simpson Bay?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 7h 38m, compared with 7h 42m via Baltimore/Washington (BWI) and 8h 09m via Orlando (MCO).

  • What is the time difference between Chicago and Simpson Bay?

    Simpson Bay is 1 hour ahead of Chicago (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
    · Ace
    · Right Cars
    · Europcar
    · Budget
    · Alamo

  • How much should I expect to pay for a Chicago to Simpson Bay flight?

    Round-trip flights from Chicago to Simpson Bay range from $517 to $797, with an average of $667 over the past 12 months. Anything below $517 counts as a good deal.

  • Which airlines offer Wi-Fi on Chicago to Simpson Bay flights?

    Two airlines offer in-flight Wi-Fi on Chicago to Simpson Bay flights:

    • • American Airlines
    • • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Chicago to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Monday departure instead of Saturday. On this route, Monday flights average $509 - about $204 less than Saturday (29% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 8 weeks before you fly. On this route, that window historically saves about 37% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to Simpson Bay trip for February. Fares historically average $482 round-trip in that month - typically $309 less than the most expensive month, which is December (based on the last 12 months).
  • If arriving on time is high on your priority list, American Airlines is the strongest pick on this route. 82% of American Airlines flights from Chicago to Simpson Bay arrived on time in the past 3 months, slightly above the route's average on-time arrival rate of 75%. When flights on this route do arrive late, the average delay is 1 hour 57 minutes, so choosing a carrier with strong on-time performance can make a difference on tight schedules.
  • If you have the time, taking a 1-stop flight through Fort Lauderdale Airport (FLL) can be cheaper than flying direct. The cheapest layover option averages $405 round-trip on this route - about $390 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.
    - Hilton Vacation Club Flamingo Beach St. Maarten
    - The Villas at Simpson Bay Resort
    - Simpson Bay Resort Marina & Spa

Prefer to fly direct from Chicago to Simpson Bay?

 
Find which airlines fly direct from Chicago to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Chicago to Simpson Bay Princess Juliana

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Chicago

Saturday

United Airlines

United Airlines

See more direct flights

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

Information on your arrival and departure airports

Simpson Bay (SXM)