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Cheap flights from Chicago to Simpson Bay from $134

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Simpson Bay departing on 1/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Simpson Bay

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Simpson Bay that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Simpson Bay.

Cheap last minute flights

Planning a quick getaway from Chicago to Simpson Bay? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Simpson Bay, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Simpson Bay

Find recent round-trip train or bus tickets from Chicago to Simpson Bay.

All round-trip flight deals to Simpson Bay

The cheapest plane tickets to Simpson Bay found on KAYAK recently.
5:43 pm - 11:20 amORD-SXM
15h 37m2 stops
6:29 pm - 12:51 amSXM-ORD
8h 22m1 stop
Mon, Jan 13 - Sat, Jan 18
7:45 pm - 5:19 pmORD-SXM
19h 34m2 stops
6:29 pm - 8:13 pmSXM-ORD
27h 44m1 stop
Fri, Dec 13 - Fri, Dec 20
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 11:02 pmSXM-ORD
9h 37m1 stop
$402Spirit Airlines
Find Deal
Sat, Jan 4 - Fri, Jan 10
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 11:02 pmSXM-ORD
9h 37m1 stop
$404Spirit Airlines
Find Deal
Sat, Jan 4 - Fri, Jan 10
6:00 am - 3:16 pmMDW-SXM
7h 16m1 stop
1:40 pm - 10:20 pmSXM-MDW
10h 40m1 stop
$630Delta
Find Deal
Tue, Jan 7 - Tue, Jan 14
5:45 am - 3:11 pmORD-SXM
7h 26m1 stop
1:40 pm - 11:59 pmSXM-ORD
12h 19m1 stop
$630Delta
Find Deal
Wed, Jan 1 - Fri, Jan 10
8:25 pm - 2:00 pmORD-SXM
15h 35m2 stops
2:55 pm - 12:09 amSXM-ORD
11h 14m1 stop
$634American Airlines
Find Deal
Sat, Jan 25 - Tue, Jan 28
8:20 pm - 11:44 amORD-SXM
14h 24m2 stops
4:00 pm - 7:23 amSXM-ORD
16h 23m2 stops
$659American Airlines
Find Deal
Mon, Mar 10 - Mon, Mar 24
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$665United Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
4:55 pm - 11:29 pmSXM-ORD
8h 34m1 stop
$728United Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
1:00 pm - 11:20 amORD-SXM
20h 20m1 stop
Mon, Jan 6
4:41 pm - 11:20 amORD-SXM
16h 39m2 stops
Mon, Jan 6
3:22 pm - 11:20 amORD-SXM
41h 58m2 stops
Tue, Feb 4
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
$183Spirit Airlines
Find Deal
Wed, Dec 4
8:30 am - 2:16 pmORD-SXM
27h 46m1 stop
$185Spirit Airlines
Find Deal
Thu, Jan 16
5:22 am - 3:02 pmORD-SXM
8h 40m2 stops
$312American Airlines
Find Deal
Wed, Mar 12
6:00 am - 3:11 pmMDW-SXM
7h 11m1 stop
$334Delta
Find Deal
Sat, Jan 4
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
$378United Airlines
Find Deal
Sat, Jan 4
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
$402Delta
Find Deal
Wed, Dec 4
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
$468United Airlines
Find Deal
Sat, Dec 7
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 9:20 amSXM-ORD
19h 55m1 stop
$891Spirit Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
1:25 pm - 8:02 amSXM-ORD
20h 37m2 stops
Mon, Nov 25 - Sat, Nov 30
5:00 am - 10:45 amORD-SXM
27h 45m3 stops
1:25 pm - 8:02 amSXM-ORD
20h 37m2 stops
$1,026
Find Deal
Mon, Nov 25 - Sat, Nov 30
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
6:10 pm - 1:09 amSXM-ORD
32h 59m3 stops
$1,032
Find Deal
Mon, Nov 25 - Sat, Nov 30
8:25 pm - 2:19 pmORD-SXM
15h 54m1 stop
4:25 pm - 11:55 pmSXM-ORD
9h 30m1 stop
$1,045American Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
8:28 pm - 2:19 pmORD-SXM
15h 51m2 stops
3:20 pm - 11:55 pmSXM-ORD
10h 35m1 stop
$1,049American Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
4:55 pm - 11:20 pmSXM-ORD
8h 25m1 stop
$1,200United Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
8:25 pm - 3:55 pmORD-SXM
17h 30m2 stops
5:45 pm - 7:56 amSXM-ORD
16h 11m2 stops
$1,230Air Canada
Find Deal
Sat, Nov 23 - Sat, Nov 30
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:51 pm - 6:45 pmSXM-ORD
5h 54mnonstop
$1,270United Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
3:27 pm - 9:46 pmSXM-MDW
8h 19m1 stop
$1,896Delta
Find Deal
Mon, Nov 25 - Sat, Nov 30
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$665United Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$729Lufthansa
Find Deal
Sun, Jan 5 - Sun, Jan 12
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$730United Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$755United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 18
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$805United Airlines
Find Deal
Sun, Jan 12 - Sat, Jan 18
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$838United Airlines
Find Deal
Sat, Jan 4 - Sun, Jan 12
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$850United Airlines
Find Deal
Sun, Mar 2 - Sat, Mar 8
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$933United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 25
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$1,010United Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 1
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
1:16 pm - 6:10 pmSXM-ORD
5h 54mnonstop
$1,122United Airlines
Find Deal
Sat, Mar 8 - Sat, Mar 22

Spirit Airlines flights from Chicago to Simpson Bay

Our best Spirit Airlines deals on Chicago to Simpson Bay flight tickets
Spirit Airlines
Jan 4
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
SXM2:30 pmSimpson Bay Princess Juliana
Jan 10
SXM3:25 pmSimpson Bay Princess Juliana
9h 37m
1 stop
ORD11:02 pmChicago O'Hare Intl
Spirit Airlines
Jan 4
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
SXM2:30 pmSimpson Bay Princess Juliana
Jan 10
SXM3:25 pmSimpson Bay Princess Juliana
9h 37m
1 stop
ORD11:02 pmChicago O'Hare Intl
Spirit Airlines
Jan 8
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
SXM2:30 pmSimpson Bay Princess Juliana
Jan 15
SXM3:25 pmSimpson Bay Princess Juliana
9h 37m
1 stop
ORD11:02 pmChicago O'Hare Intl

Air Canada flights from Chicago to Simpson Bay

Our best Air Canada deals on Chicago to Simpson Bay flight tickets
Air Canada
Dec 7
ORD6:10 pmChicago O'Hare Intl
19h 45m
2 stops
SXM3:55 pmSimpson Bay Princess Juliana
Dec 14
SXM5:45 pmSimpson Bay Princess Juliana
16h 11m
2 stops
ORD7:56 amChicago O'Hare Intl
Air Canada
Dec 7
ORD6:38 pmChicago O'Hare Intl
19h 17m
2 stops
SXM3:55 pmSimpson Bay Princess Juliana
Dec 14
SXM5:45 pmSimpson Bay Princess Juliana
16h 11m
2 stops
ORD7:56 amChicago O'Hare Intl
Air Canada
Dec 1
ORD2:00 pmChicago O'Hare Intl
24h 15m
2 stops
SXM4:15 pmSimpson Bay Princess Juliana
Dec 6
SXM5:15 pmSimpson Bay Princess Juliana
17h 42m
1 stop
ORD8:57 amChicago O'Hare Intl

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Chicago to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

September. The cheapest time of year to fly to Simpson Bay from Chicago is September. Most expensive is March

What is the cheapest day to depart Chicago for Simpson Bay?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Saturday

When is the cheapest time to fly from Chicago to Simpson Bay?

At noon. Chicago to Simpson Bay flights are approximately 43% more expensive in the morning than at noon

What is the cheapest Chicago to Simpson Bay flight route?

Chicago O'Hare Intl - Simpson Bay Princess Juliana. Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago - Simpson Bay flight prices

How far in advance should you book Chicago to Simpson Bay flights?

54 days before. The cheapest time to buy a flight from Chicago to Simpson Bay is approximately 54 days to departure

Can stopping save me money on Chicago to Simpson Bay flights?

You could potentially save up to 64% on your flight if you consider stops on a Chicago to Simpson Bay flight.

How have Chicago to Simpson Bay flight prices changed over time?


When to book flights from Chicago to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Simpson Bay (CHI to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Simpson Bay

Best Price Found

$134

Fastest flight time

5h 06m

Direct flights

Mon and Sun

Airports in Simpson Bay

1 airport
The best one-way flight to Simpson Bay from Chicago in the past 72 hours is $134. The best round-trip flight deal from Chicago to Simpson Bay found on momondo in the last 72 hours is $355.
The fastest flight from Chicago to Simpson Bay takes 5h 06m
Direct flights go from Chicago to Simpson Bay on Monday and Sunday. Airlines offering direct flights are: United Airlines and Lufthansa.
There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

  • How far is Chicago to Simpson Bay Princess Juliana by plane?

    A flight from Chicago to Simpson Bay Princess Juliana will travel around 2188.1 mi. Typically, this will take 5h 07m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to Simpson Bay Princess Juliana Airport?

    Prices for flights from Chicago to Simpson Bay Princess Juliana Airport were last updated today.

  • How many operators does momondo search for flights from Chicago to Simpson Bay Princess Juliana Airport?

  • How old do you have to be to fly from Chicago to Simpson Bay Princess Juliana Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Simpson Bay Princess Juliana Airport.

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The required travel and health documents for your Simpson Bay Princess Juliana Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Simpson Bay?

  • What is the most popular airline from Chicago to Simpson Bay?


Best airlines flying from Chicago to Simpson Bay

Compare and see reviews for airlines that fly from Chicago to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $263Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $553Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $554Free CancellationRating
8.0
8,759 reviews
Search Delta flights
United AirlinesPriceFrom $617Free CancellationRating
7.4
9,173 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Simpson Bay?

It is quick and easy to find Chicago to Simpson Bay flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Simpson Bay that suits you.

Can I find flights from Chicago to Simpson Bay with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Simpson Bay flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Simpson Bay?

Once you have performed a search for Chicago to Simpson Bay flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Simpson Bay right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.


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