Cheap flights from Chicago to Simpson Bay from $158
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 7/9. 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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Spirit Airlines flights from Chicago to Simpson Bay
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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 $609. If you aren’t able to travel to Simpson Bay during the month of September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $637.
What is the cheapest day to depart on your flight to Simpson Bay?
Our data shows that Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $644. Flights from Chicago to Simpson Bay on a Saturday will generally be more expensive and average around $943. 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 $929.
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?
You are more likely to see cheaper flights to Simpson Bay from Chicago when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $739 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Chicago for as low as $603 on momondo.
What cabin class options are available on Chicago to Simpson Bay Princess Juliana flights?
There are 2 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.
What is the cheapest airline that flies from Chicago to Simpson Bay Princess Juliana?
Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from Chicago to Simpson Bay Princess Juliana
What airlines fly to Simpson Bay?
American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Simpson Bay from Chicago according to our data. American Airlines is the first choice among our users, with 49% 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.
When to book flights from Chicago to Simpson Bay
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
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 35m 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?
As of June 2025, there are 4 operators available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Simpson Bay is Boeing 737-700, representing 66.04% of all bookings. The subsequent popular models are Airbus A319 at 32.08% and Boeing 737 MAX 8 at 1.89%.
What is the most popular airline from Chicago to Simpson Bay?
momondo data reveals that the most frequently booked airline on the route from Chicago to Simpson Bay is American Airlines, representing 50% of all bookings. The subsequent popular airlines are United Airlines at 21%, Delta at 15%, and Spirit Airlines at 14%.
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 | ||
|---|---|---|---|---|---|
| PriceFrom $330 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $554 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $615 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $654 | Free Cancellation | Rating 7.4 8,790 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 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.