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Cheap flights from Chicago to Simpson Bay from $123

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 1/24. 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.
1:44 pm - 11:20 amORD-SXM
19h 36m1 stop
6:29 pm - 12:51 amSXM-ORD
8h 22m1 stop
Sat, Feb 1 - Sat, Feb 8
1:44 pm - 11:20 amORD-SXM
19h 36m1 stop
6:29 pm - 12:51 amSXM-ORD
8h 22m1 stop
Sat, Feb 1 - Sat, Feb 8
5:11 am - 2:26 pmORD-SXM
7h 15m1 stop
3:43 pm - 11:32 pmSXM-ORD
9h 49m1 stop
$384Spirit Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 29
5:11 am - 2:26 pmORD-SXM
7h 15m1 stop
3:43 pm - 11:32 pmSXM-ORD
9h 49m1 stop
$394Spirit Airlines
Find Deal
Fri, Jan 10 - Sat, Jan 18
4:13 pm - 5:09 pmMDW-SXM
22h 56m2 stops
6:31 pm - 3:13 pmSXM-MDW
22h 42m2 stops
$472Frontier
Find Deal
Thu, Feb 13 - Mon, Feb 17
5:45 pm - 5:15 pmMDW-SXM
22h 30m2 stops
6:35 pm - 1:31 pmSXM-MDW
19h 56m2 stops
$564Frontier
Find Deal
Sun, Mar 23 - Mon, Mar 31
5:10 am - 2:00 pmORD-SXM
6h 50m1 stop
5:19 pm - 8:59 amSXM-ORD
17h 40m1 stop
$630American Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:00 am - 3:16 pmMDW-SXM
7h 16m1 stop
1:40 pm - 10:20 pmSXM-MDW
10h 40m1 stop
$630Delta
Find Deal
Wed, Jan 22 - Wed, Jan 29
5:10 am - 4:11 pmORD-SXM
9h 01m2 stops
5:19 pm - 8:30 amSXM-ORD
17h 11m2 stops
$634American Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:00 am - 3:16 pmMDW-SXM
7h 16m1 stop
1:40 pm - 10:20 pmSXM-MDW
10h 40m1 stop
$655Delta
Find Deal
Thu, Feb 27 - Tue, Mar 4
10:02 pm - 5:19 pmORD-SXM
17h 17m2 stops
$123Frontier
Find Deal
Fri, Jan 24
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
$155Spirit Airlines
Find Deal
Wed, Jan 8
10:02 pm - 11:13 amORD-SXM
35h 11m3 stops
Fri, Jan 24
4:18 pm - 11:13 amORD-SXM
40h 55m3 stops
Sun, Jan 19
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
$308United Airlines
Find Deal
Sun, Jan 19
6:30 pm - 2:00 pmORD-SXM
17h 30m1 stop
$312American Airlines
Find Deal
Sat, Jan 18
6:00 am - 2:00 pmMDW-SXM
7h 00m1 stop
$312Delta
Find Deal
Wed, Mar 26
6:00 am - 4:20 pmMDW-SXM
8h 20m1 stop
$382Delta
Find Deal
Sat, Jan 18
6:37 am - 4:09 pmORD-SXM
7h 32m1 stop
$493American Airlines
Find Deal
Mon, Dec 23
8:45 am - 2:52 pmORD-SXM
5h 07mnonstop
$565United Airlines
Find Deal
Sat, Mar 15
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
5:15 pm - 7:32 pmSXM-ORD
28h 17m1 stop
Fri, Dec 20 - Wed, Dec 25
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
5:15 pm - 7:32 pmSXM-ORD
28h 17m1 stop
Fri, Dec 20 - Wed, Dec 25
12:09 pm - 2:30 pmORD-SXM
24h 21m1 stop
3:25 pm - 7:51 pmSXM-ORD
30h 26m1 stop
$969Spirit Airlines
Find Deal
Thu, Dec 19 - Fri, Dec 27
12:09 pm - 2:30 pmORD-SXM
24h 21m1 stop
3:25 pm - 7:47 amSXM-ORD
18h 22m2 stops
$973Spirit Airlines
Find Deal
Thu, Dec 19 - Fri, Dec 27
6:00 am - 3:11 pmMDW-SXM
7h 11m1 stop
1:50 pm - 10:06 pmSXM-MDW
10h 16m1 stop
$1,010Delta
Find Deal
Thu, Dec 19 - Fri, Dec 27
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$1,070United Airlines
Find Deal
Sat, Dec 21 - Sat, Dec 28
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
4:55 pm - 11:25 pmSXM-ORD
8h 30m1 stop
$1,130United Airlines
Find Deal
Sat, Dec 21 - Sat, Dec 28
6:00 am - 3:11 pmMDW-SXM
7h 11m1 stop
1:50 pm - 10:06 pmSXM-MDW
10h 16m1 stop
$1,155Delta
Find Deal
Thu, Dec 19 - Fri, Dec 27
5:02 am - 4:09 pmORD-SXM
9h 07m2 stops
3:20 pm - 7:19 amSXM-ORD
17h 59m2 stops
$1,164American Airlines
Find Deal
Fri, Dec 20 - Wed, Dec 25
6:55 pm - 12:30 pmORD-SXM
15h 35m1 stop
5:14 pm - 12:26 amSXM-ORD
9h 12m1 stop
$1,165American Airlines
Find Deal
Fri, Dec 20 - Tue, Dec 31
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$731United Airlines
Find Deal
Sun, Jan 19 - Sun, Jan 26
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$798United Airlines
Find Deal
Sat, Jan 11 - Sun, Jan 19
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$813United Airlines
Find Deal
Sun, Feb 2 - Sun, Feb 9
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$838United Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
8:45 am - 2:52 pmORD-SXM
5h 07mnonstop
1:16 pm - 6:10 pmSXM-ORD
5h 54mnonstop
$858United Airlines
Find Deal
Sun, Mar 9 - Sun, Mar 16
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$883United Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$895United 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, Feb 22 - Sat, Mar 1
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$975United 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
$1,056Air Canada
Find Deal
Sat, Feb 1 - Sat, Feb 8

American Airlines flights from Chicago to Simpson Bay

Our best American Airlines deals on Chicago to Simpson Bay flight tickets
American Airlines
Jan 14
ORD5:10 amChicago O'Hare Intl
6h 50m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Jan 21
SXM5:19 pmSimpson Bay Princess Juliana
17h 40m
1 stop
ORD8:59 amChicago O'Hare Intl
American Airlines
Jan 14
ORD5:10 amChicago O'Hare Intl
9h 01m
2 stops
SXM4:11 pmSimpson Bay Princess Juliana
Jan 21
SXM5:19 pmSimpson Bay Princess Juliana
17h 11m
2 stops
ORD8:30 amChicago O'Hare Intl
American Airlines
Jan 19
ORD8:40 pmChicago O'Hare Intl
15h 20m
2 stops
SXM2:00 pmSimpson Bay Princess Juliana
Jan 26
SXM4:18 pmSimpson Bay Princess Juliana
17h 06m
2 stops
ORD7:24 amChicago O'Hare Intl

Spirit Airlines flights from Chicago to Simpson Bay

Our best Spirit Airlines deals on Chicago to Simpson Bay flight tickets
Spirit Airlines
Jan 22
ORD5:11 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:26 pmSimpson Bay Princess Juliana
Jan 29
SXM3:43 pmSimpson Bay Princess Juliana
9h 49m
1 stop
ORD11:32 pmChicago O'Hare Intl
Spirit Airlines
Jan 10
ORD5:11 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:26 pmSimpson Bay Princess Juliana
Jan 18
SXM3:43 pmSimpson Bay Princess Juliana
9h 49m
1 stop
ORD11:32 pmChicago O'Hare Intl
Spirit Airlines
Jan 24
ORD5:11 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:26 pmSimpson Bay Princess Juliana
Feb 1
SXM3:43 pmSimpson Bay Princess Juliana
9h 49m
1 stop
ORD11:32 pmChicago 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 typical price of a round-trip flight between Chicago and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Chicago to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $604. If you aren’t able to travel to Simpson Bay during the month of September, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $609.

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Wednesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $619. Flights from Chicago to Simpson Bay on a Saturday will generally be more expensive and average around $827. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is at noon. momondo users have found flights departing from Chicago to Simpson Bay at noon for as low as $417. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $753.

What is the cheapest Chicago to Simpson Bay Princess Juliana flight route?

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

How far in advance should I book a flight to Simpson Bay?

Most flyers found that booking tickets 21 days in advance of their planned departure date is the best time to get cheap flights to Simpson Bay. During this timeframe, flight prices are around $756. However, in the past 72 hours, people saw flights from Chicago for as low as $323.

What cabin class options are available on Chicago to Simpson Bay Princess Juliana flights?

There are 3 cabin classes available to choose from on Chicago to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 63% 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

$123

Fastest flight time

5h 07m

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 $123. The best round-trip flight deal from Chicago to Simpson Bay found on momondo in the last 72 hours is $350.
The fastest flight from Chicago to Simpson Bay takes 5h 07m
Direct flights go from Chicago to Simpson Bay on Monday and Sunday. Airlines offering direct flights are: United Airlines and Air Canada.
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 6h 50m 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 $259Free CancellationRating
6.3
8,119 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $553Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $554Free CancellationRating
8.0
8,604 reviews
Search Delta flights
United AirlinesPriceFrom $633Free CancellationRating
7.4
9,059 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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