Cheap flights from Illinois to Simpson Bay from $147
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Simpson Bay departing on 12/12. 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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Fly from
Fly to
Route
Depart
Return
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Thu 12/3
1:55 pm-2:45 pm
2 stops46h 50m
Simpson Bay Princess Juliana
Sun 12/6
4:45 pm-7:58 pm
1 stop29h 13m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 12/9
1:55 pm-2:45 pm
2 stops22h 50m
Simpson Bay Princess Juliana
Sun 12/13
4:45 pm-9:08 am
1 stop18h 23m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 12/9
7:05 am-2:45 pm
1 stop29h 40m
Simpson Bay Princess Juliana
Sun 12/13
4:45 pm-7:58 pm
1 stop29h 13m
MolineSimpson Bay
MLI Moline Quad-City - SXM Simpson Bay Princess Juliana
MLISXM
Moline Quad-City
Sat 12/5
4:42 pm-2:27 pm
2 stops19h 45m
Simpson Bay Princess Juliana
Sat 12/12
4:30 pm-11:02 am
2 stops20h 32m
PeoriaSimpson Bay
PIA Greater Peoria - SXM Simpson Bay Princess Juliana
PIASXM
Greater Peoria
Sat 1/16
6:37 pm-2:59 pm
2 stops18h 22m
Simpson Bay Princess Juliana
Sat 1/23
1:34 pm-11:47 am
2 stops24h 13m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 10/28
5:27 am-1:40 pm
1 stop7h 13m
Simpson Bay Princess Juliana
Wed 11/4
4:05 pm-11:57 pm
1 stop9h 52m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 10/28
5:27 am-1:40 pm
1 stop7h 13m
Simpson Bay Princess Juliana
Thu 11/5
4:05 pm-11:57 pm
1 stop9h 52m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Mon 1/4
8:40 am-3:57 pm
Nonstop5h 17m
Simpson Bay Princess Juliana
Thu 1/7
5:00 pm-11:44 pm
1 stop8h 44m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sun 12/20
9:35 pm-1:50 pm
1 stop14h 15m
Simpson Bay Princess Juliana
Sun 12/27
5:00 pm-12:01 am
1 stop9h 01m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sat 12/19
7:55 pm-12:21 pm
1 stop14h 26m
Simpson Bay Princess Juliana
Sun 12/27
2:20 pm-11:33 pm
1 stop11h 13m
See travel insights to Simpson Bay from
How to get the cheapest flight ticket from Illinois 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 to Simpson Bay?
In general, February is the cheapest month to fly from Illinois to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $573. If you aren’t able to travel to Simpson Bay during the month of February, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $589.
What is the cheapest day to depart on your flight to Simpson Bay?
Our data shows that Sunday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $553. Flights from Illinois to Simpson Bay on a Saturday will generally be more expensive and average around $780. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.
What is the cheapest Illinois to Simpson Bay Princess Juliana flight route?
Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Illinois - Simpson Bay Princess Juliana flight prices
How far in advance should I book a flight from Illinois to Simpson Bay?
You are more likely to see cheaper flights to Simpson Bay from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $689 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Illinois for as low as $532 on momondo.
What cabin class options are available on Illinois to Simpson Bay flights?
There are 4 cabin classes available to choose from on Illinois to Simpson Bay 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 Illinois to Simpson Bay flights?
You could potentially save up to 41% on your flight if you consider stops on a Illinois to Simpson Bay flight.
What is the cheapest airline that flies from Illinois to Simpson Bay Princess Juliana?
Air Canada, United Airlines, and Delta are the most popular carriers operating from Illinois to Simpson Bay Princess Juliana
What airlines fly to Simpson Bay?
American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Simpson Bay from Illinois according to our data. American Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 4 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.
Cheap Illinois to Simpson Bay flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Illinois to Simpson Bay
Frequently asked questions about flying from Illinois to Simpson Bay
When did momondo last update prices for flights from Illinois to Simpson Bay Princess Juliana Airport?
Prices for flights from Illinois to Simpson Bay Princess Juliana Airport are updated daily.
How many operators does momondo search for flights from Illinois to Simpson Bay Princess Juliana Airport?
There are 4 operators available for flights from Illinois to Simpson Bay Princess Juliana Airport as of October 2026.
How old do you have to be to fly from Illinois to Simpson Bay Princess Juliana Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois 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 Illinois to Simpson Bay?
momondo data reveals that the most frequently booked plane model on the route from Illinois to Simpson Bay is Boeing 737 MAX 8, representing 63.22% of all bookings. The subsequent popular models are Airbus A319 at 22.99%, Boeing 737-700 at 6.90%, and Airbus A318/A319/A320/A321 at 2.30%.
Best airlines flying from Illinois to Simpson Bay
Compare and see reviews for airlines that fly from Illinois to Simpson Bay with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $240 | Free Cancellation | Rating 7.8 8,645 reviews | |||
| PriceFrom $389 | Free Cancellation | Rating 7.1 3,049 reviews | |||
| PriceFrom $410 | Free Cancellation | Rating 7.4 10,319 reviews | |||
| PriceFrom $501 | Free Cancellation | Rating 7.0 12,145 reviews |
Traveling to a place near Simpson Bay?
Book flights to Simpson Bay if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Illinois to Simpson Bay?
Finding the right flight to Simpson Bay from Illinois is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Simpson Bay quick and easy, saving you time and money.
Can I find flights from Illinois to Simpson Bay with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Illinois to Simpson Bay flights to just show those with flexible booking policies.
How can momondo help me find flights from Illinois to Simpson Bay?
momondo helps you find the best flight between Illinois and Simpson Bay by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Illinois to Simpson Bay right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Illinois 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.