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CHI - SXM

$142 Find Cheap Flights from Chicago to Simpson Bay - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$363
Typical prices: $517-$797
Air Canada
Mon 12/10Fri 12/14
ORD - SXM • 1 stop
Cheapest non-stop
$568
Typical prices: $612-$950
United Airlines
Mon 12/24Sun 12/30
ORD - SXM • Non-stop
Nonstop flights
1 day a week
You can fly direct with United Airlines and American Airlines. Average duration is 5h 18m
Direct flights
+1
Direct flights
+1
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 $418 (round-trip)
Charlotte Douglas (CLT)
Shortest trip • 7h 39m (one-way)
Insights
Insights
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We hope you love your trip to Simpson Bay!
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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

Thu, Dec 10 - Mon, Dec 14
Air Canada Logo
10:05 am - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
27h 40m1 stop Toronto Pearson Intl
Air Canada Logo
4:45 pm - 7:58 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
29h 13m1 stop Toronto Pearson Intl
$363Air Canada
Thu, Dec 10 - Sun, Dec 13
Air Canada Logo
1:55 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
46h 50m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
4:45 pm - 7:58 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
29h 13m1 stop Toronto Pearson Intl
$386Air Canada
Sun, Oct 18 - Wed, Oct 21
Copa Airlines Logo
3:20 pm - 11:33 amORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
19h 13m1 stop Panama City Tocumen Intl
Copa Airlines Logo
12:32 pm - 12:57 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
13h 25m1 stop Panama City Tocumen Intl
$477Copa Airlines
Thu, Nov 5 - Sun, Nov 8
Copa Airlines Logo
2:13 pm - 11:30 amORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
19h 17m1 stop Panama City Tocumen Intl
Copa Airlines Logo
12:25 pm - 12:11 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
13h 46m1 stop Panama City Tocumen Intl
$477Copa Airlines
Mon, Oct 12 - Fri, Oct 16
American Airlines Logo
6:14 am - 3:39 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
8h 25m1 stop Miami
American Airlines Logo
4:39 pm - 12:38 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
8h 59m1 stop Miami
$481American Airlines
Mon, Oct 12 - Fri, Oct 16
American Airlines Logo
6:14 am - 3:39 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
8h 25m1 stop Miami
American Airlines Logo
4:39 pm - 7:27 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
15h 48m2 stops Miami Washington, D.C. Reagan-National
$481American Airlines
Mon, Oct 12 - Fri, Oct 16
Delta Logo
6:04 am - 1:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 36m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:05 pm - 10:33 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 28m1 stop Atlanta Hartsfield-Jackson
$489Delta
Mon, Nov 30 - Wed, Dec 9
Delta Logo
5:30 am - 2:37 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
7h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:05 pm - 8:46 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
18h 41m1 stop Atlanta Hartsfield-Jackson
$489Delta
Tue, Dec 29 - Thu, Jan 7
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 - 9:44 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
18h 44m1 stop Washington, D.C. Dulles Intl
$492United Airlines
Tue, Dec 29 - Thu, Jan 7
United Airlines Logo
9:35 pm - 1:50 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
14h 15m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
5:00 pm - 11:59 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
8h 59m1 stop Washington, D.C. Dulles Intl
$496United 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 with more confidence.

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

Round-trip flights from Chicago to Simpson Bay typically range from $517 to $797. The lowest price found in the past 5 days was $363, 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?

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

What’s 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 flights 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.

Find deals

Key details for Chicago to Simpson Bay flights

Low season

August

Cheapest flight

$142
Beat the crowds with an average 64% drop in travelers.
The most popular month to fly with an average 58% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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 8:10 am and lands at 1:28 pm
    • Latest: departs at 8:40 am and lands at 1:58 pm.

    The flight takes about 5h 18m.

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

    Two cabin classes are available on flights from Chicago to Simpson Bay:

    • Economy Class
    • Business Class

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

    A nonstop flight from Chicago to Simpson Bay takes 5h 18m, covering 2,188 miles.

  • 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 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.

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

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

  • 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 $418 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 airlines offer Wi-Fi on Chicago to Simpson Bay flights?

    American Airlines is the only airline on the Chicago to Simpson Bay route offering in-flight Wi-Fi. Pricing depends on fare class.

  • 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 $194, which is 40% below the typical average for this route.

  • 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

  • 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).

  • What time of day has the fewest delays on flights from Chicago to Simpson Bay?

    Morning flights have the fewest delays on this route.

  • 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 1h 57m.

  • 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) - 35% of one-stop connections
    • Miami (MIA) - 32% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 13% of one-stop connections
    • Charlotte Douglas (CLT) - 10% of one-stop connections

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

    Yes. Flexible dates can save you up to 29% on flights from Chicago to Simpson Bay. 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.

  • What airlines fly from Chicago to Simpson Bay?

    2 airlines operate flights between Chicago and Simpson Bay. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines

  • 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 39m, compared with 7h 42m via Baltimore/Washington (BWI) and 8h 08m 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.

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

    Among airlines operating Chicago to Simpson Bay flights:

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

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

  • 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
    • Alaska Airlines: a cabin bag and a checked bag in Business Class
    • United Airlines: a cabin bag and a checked bag in Business Class

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

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 are flexible, aim for a Monday departure and avoid flying on Saturday. On this route, Monday flights average $509, about $204 less than Saturday fares (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).
  • For the best chance of arriving on time, fly with American Airlines. Over the past three months, 82% of American Airlines flights from Chicago to Simpson Bay arrived on time, slightly above the route average of 75%. When flights on this route arrive late, they're delayed by an average of 1h 57m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • 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 $418 round-trip on this route - about $377 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.

    • Simpson Bay Resort Marina & Spa
    • Hilton Vacation Club Flamingo Beach St. Maarten
    • The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

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

More options for your flight from Chicago to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental

Car rentals in Simpson Bay
Hotels in Simpson Bay
Vacations in Simpson Bay