SXM - ORD

$191 Find Cheap Flights from Simpson Bay to Chicago - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$367
Typical prices: $586-$792
Air Canada
Wed 10/31Wed 11/7
SXM - ORD • 1 stop
Cheapest non-stop
$618
Typical prices: $610-$1,734
United Airlines
Wed 11/7Wed 11/14
SXM - ORD • Non-stop
Nonstop flights
You can fly direct with United Airlines and American Airlines. Average duration is 5h 59m
Direct flights
+1
Direct flights
+1
When to travel
Cheapest • 50% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $431 (round-trip)
Shortest trip • 8h 24m (one-way)
Insights
Insights
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Booking Insights
Flight Deals

Cheap Flights from Simpson Bay to O'Hare Intl (SXM-ORD)

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

Recent round-trip flight deals from Simpson Bay to O'Hare Intl

Sat, Oct 31 - Sat, Nov 7
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
Air Canada Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$367Air Canada
Sat, Oct 31 - Sat, Nov 7
Air Canada Logo
2:40 pm - 10:23 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
20h 43m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$376Air Canada
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
9:21 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 24m1 stop Toronto Pearson Intl
$400Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
9:21 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 24m1 stop Toronto Pearson Intl
$401Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
10:15 am - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
27h 30m1 stop Toronto Pearson Intl
$403Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
4:16 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
46h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$406Multiple Airlines
Fri, Oct 30 - Fri, Nov 6
Air Canada Logo
3:45 pm - 1:13 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
22h 28m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 05m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$422Air Canada
Fri, Oct 30 - Fri, Nov 6
Air Canada Logo
3:45 pm - 11:07 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
20h 22m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:40 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 05m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$425Air Canada
Sat, Nov 7 - Sat, Nov 14
Air Canada Logo
3:45 pm - 9:23 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
19h 38m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
4:30 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
21h 15m1 stop Toronto Pearson Intl
$431Air Canada
Sat, Nov 7 - Sat, Nov 14
Air Canada Logo
3:45 pm - 9:23 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
19h 38m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
3:45 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$434Air Canada
Booking Insights

Price, demand and travel trends for Simpson Bay to Chicago O'Hare Intl Airport flights

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

How much is a round-trip flight from Simpson Bay to Chicago O'Hare Intl Airport?

Round-trip flights from Simpson Bay to Chicago O'Hare Intl Airport start at $367. Prices are below average for this route right now, with typical round-trip fares ranging from $586 to $792. The lowest price found in the past 5 days was $367 on Air Canada.

Key details for Simpson Bay to Chicago O'Hare Intl Airport flights

Low season

May

Cheapest flight

$191
Flight from Simpson Bay to Chicago O'Hare Intl Airport

When to book flights from Simpson Bay to O'Hare Intl

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

Your Simpson Bay to Chicago O'Hare Intl Airport 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 Simpson Bay to Chicago O'Hare Intl Airport flights?

    Among airlines operating Simpson Bay to Chicago O'Hare Intl Airport flights:

    • United Airlines: offers free seat selection

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

  • What airlines are available from Simpson Bay to Chicago O'Hare Intl Airport?

    2 airlines operate flights between Simpson Bay and Chicago O'Hare Intl Airport. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines

  • Which airports can I use when flying from Simpson Bay to Chicago O'Hare Intl Airport?

    Flights from Simpson Bay to Chicago O'Hare Intl Airport usually depart from Simpson Bay Princess Juliana (SXM) and arrive at Chicago O'Hare Intl (ORD).

  • Which airlines include bags at no extra cost on Simpson Bay to Chicago O'Hare Intl Airport 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 Business Class
    • United Airlines: 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 Simpson Bay to Chicago O'Hare Intl Airport?

    Two cabin classes are available on flights from Simpson Bay to Chicago O'Hare Intl Airport:

    • Economy Class
    • Business Class

  • How much can I save by taking a layover when flying from Simpson Bay to Chicago O'Hare Intl Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $431 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $902 for nonstop.

  • What is the standard checked-bag allowance on flights from Simpson Bay to Chicago O'Hare Intl Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $70–$70 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Simpson Bay to Chicago O'Hare Intl Airport?

    The Boeing 737-700 family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Airbus A319 variants.

  • Which airports do connecting flights from Simpson Bay to Chicago O'Hare Intl Airport pass through?

    One-stop flights from Simpson Bay to Chicago O'Hare Intl Airport most commonly connect through:

    • Fort Lauderdale (FLL) - 44% of one-stop connections
    • Miami (MIA) - 44% of one-stop connections
    • New York John F Kennedy Intl (JFK) - 8% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 4% 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 Simpson Bay to Chicago O'Hare Intl Airport?

    Yes. Being flexible with your travel dates can save you up to 27% on the Simpson Bay to Chicago O'Hare Intl Airport route. Wednesday is the cheapest departure day at $580 round-trip on average, while Monday is the most expensive at $792, a difference of $212. 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 popular places can I visit in Chicago O'Hare Intl Airport?

    Some of the most popular sights in Chicago O'Hare Intl Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

  • What are the earliest and latest flights from Simpson Bay to Chicago O'Hare Intl Airport?

    These are the earliest and latest flight times available from Simpson Bay to Chicago O'Hare Intl Airport:

    • Earliest: departs at 1:10 pm and lands at 7:09 pm
    • Latest: departs at 4:25 pm and lands at 10:24 pm.

    The flight takes about 5h 59m.

  • How long is a flight from Simpson Bay to Chicago O'Hare Intl Airport?

    A nonstop flight from Simpson Bay to Chicago O'Hare Intl Airport takes 5h 59m, covering 2,204 miles.

  • Do I need a passport to fly from Simpson Bay to Chicago O'Hare Intl Airport?

    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.

  • Have flight prices from Simpson Bay to Chicago O'Hare Intl Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $367 to $3,588. That means the highest observed fare was about 10x higher than the lowest one.

  • How are flight prices from Simpson Bay to Chicago O'Hare Intl Airport looking right now?

    One-way fares from Simpson Bay to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about $212, which is 60% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Simpson Bay to Chicago O'Hare Intl Airport?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 7h 37m, compared with 8h 24m via Miami (MIA) and 11h 20m via Fort Lauderdale (FLL).

  • What is the time difference between Simpson Bay and Chicago O'Hare Intl Airport?

    Chicago O'Hare Intl Airport is 1 hour behind Simpson Bay (Central Time vs Atlantic Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago O'Hare Intl Airport (ORD)?

    Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates starting from around $17 for economy cars. Top options include:
    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Dollar
    • Ace

  • How much should I expect to pay for a Simpson Bay to Chicago O'Hare Intl Airport flight?

    Round-trip flights from Simpson Bay to Chicago O'Hare Intl Airport range from $586 to $792, with an average of $722 over the past 12 months. Anything below $586 counts as a good deal.

Your guide to booking Simpson Bay to Chicago O'Hare Intl Airport 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 Wednesday departure instead of Monday. On this route, Wednesday flights average $580 - about $212 less than Monday (27% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Simpson Bay to Chicago O'Hare Intl Airport trip for December. Fares historically average $364 round-trip in that month - typically $1,978 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $431 round-trip on this route - about $471 less than direct flights (based on the last 12 months).

Prefer to fly direct from Simpson Bay to Chicago?

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

Direct departures

Simpson Bay Princess Juliana to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to Simpson Bay Princess Juliana

Saturday

United Airlines

United Airlines

See more direct flights

More options for your flight from Simpson Bay to O'Hare Intl

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