CHI - SXM

$94 Find Cheap Flights from Chicago to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Simpson Bay departing on 1/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Simpson Bay, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$259
Overall average: $704
Spirit Airlines
Sat 1/24Mon 2/2
ORD - SXM • 1 stop
Cheapest non-stop
$547
American Airlines
Sat 2/7Sat 2/14
ORD - SXM • Non-stop
Top airlines
Spirit Airlines
Cheapest • from $261 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD-SXM
Cheapest
ORD-SXM
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 29% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 17% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
2 days a week
There are direct flights from Chicago to Simpson Bay 2 days a week: Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
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Booking Insights
Flight Deals

Cheap Flights from Chicago to Simpson Bay (CHI-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Simpson Bay

Sat, Jan 24 - Mon, Feb 2
Spirit Airlines Logo
5:15 am - 2:14 pmORD-SXM
6h 59m1 stop
Spirit Airlines Logo
3:09 pm - 11:46 pmSXM-ORD
10h 37m1 stop
$259Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Spirit Airlines Logo
5:15 am - 2:10 pmORD-SXM
6h 55m1 stop
Spirit Airlines Logo
3:15 pm - 10:03 pmSXM-ORD
8h 48m1 stop
$261Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Spirit Airlines Logo
5:15 am - 2:10 pmORD-SXM
6h 55m1 stop
Spirit Airlines Logo
3:15 pm - 10:03 pmSXM-ORD
8h 48m1 stop
$262Spirit Airlines
Find Deal
Fri, Jan 23 - Sat, Jan 31
Spirit Airlines Logo
8:22 pm - 2:14 pmORD-SXM
15h 52m1 stop
Spirit Airlines Logo
3:09 pm - 11:46 pmSXM-ORD
10h 37m1 stop
$275Spirit Airlines
Find Deal
Sat, Feb 7 - Sat, Feb 14
Multiple Airlines Logo
5:15 am - 2:10 pmORD-SXM
6h 55m1 stop
Multiple Airlines Logo
4:30 pm - 11:35 pmSXM-ORD
9h 05m1 stop
$278Multiple Airlines
Find Deal
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$287Frontier
Find Deal
Fri, Jan 23 - Sat, Jan 31
Frontier Logo
5:01 pm - 1:59 pmMDW-SXM
18h 58m1 stop
Frontier Logo
3:10 pm - 11:45 amSXM-MDW
22h 35m1 stop
$326Frontier
Find Deal
Thu, Dec 11 - Tue, Dec 16
Multiple Airlines Logo
7:44 am - 2:15 pmMDW-SXM
28h 31m2 stops
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$463Multiple Airlines
Find Deal
Sun, Jan 25 - Fri, Jan 30
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pmSXM-MDW
10h 27m1 stop
$501Delta
Find Deal
Sun, Jan 25 - Thu, Jan 29
Delta Logo
9:32 am - 12:30 pmMDW-SXM
24h 58m2 stops
Delta Logo
4:20 pm - 5:55 pmSXM-MDW
27h 35m2 stops
$506Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Simpson Bay flights

Get data-powered insights and trends into flights from Chicago to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Simpson Bay flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Simpson Bay costs $366 on the route between Chicago O'Hare Intl Airport (ORD) and Simpson Bay (SXM). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Simpson Bay?

The average price of all round-trip flights from Chicago to Simpson Bay clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Simpson Bay, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Simpson Bay is August, where tickets cost $585 (return) on average. On the other hand, the most expensive months are April and June, where the average cost of round-trip tickets is $787 and $778 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Simpson Bay, you should book around 3 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago O'Hare Airport to Simpson Bay

When to book flights from Chicago to Simpson Bay

Are your dates flexible? Find out the best times to travel from Chicago to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Simpson Bay

  • What is the cheapest flight from Chicago to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Chicago to Simpson Bay was $94 for a one-way ticket and $259 for a round-trip.

  • Do I need a passport to fly between Chicago and Simpson Bay?

    Yes, you’ll need a passport to travel to Simpson Bay from Chicago.

  • Which airports will I be using when flying from Chicago to Simpson Bay?

    On your way to Simpson Bay, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Simpson Bay Princess Juliana.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Simpson Bay?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Simpson Bay flight route.

  • Which aircraft models fly most regularly from Chicago to Simpson Bay?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago to Simpson Bay flight route.

  • Which airline alliances offer flights from Chicago to Simpson Bay?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Simpson Bay?

    You can catch a nonstop flight from Chicago to Simpson Bay on on Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to Simpson Bay, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Simpson Bay are Delta and United Airlines. With an average price for the route of $706 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $842 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $420 or less round-trip.

Prefer to fly direct from Chicago to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Simpson Bay Princess Juliana.
Find which airlines fly direct from Chicago to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Chicago to Simpson Bay Princess Juliana

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Chicago

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8010 reviews
7.3Food
8.1Boarding
8.5Crew
7.9Entertainment
7.9Comfort
Airline reviews

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

10.0 ExcellentMary Heather, Nov 2025MKE - LGA
Read more Delta reviews

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

I didn't eat, so I can't rate the food. Delayed set off was beyond

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

I hope you continue to be one of the great company

Crew are always very angry and dismissive like they seem they are being forced to work. In addition, there was a long line for the bathrooms, and only one was allowed to be used. No reason was given for only one bathroom being available; apparently, the stewardess was more interested in using the jumpseat instead of allowing the customers to use the bathroom.

Very positive in both directions. Safe travels, nice staff, lost and found in fact found my phone under my chair! I was out of cash after my NYC trip otherwise I would've offered a reward for helping my day out immensly! Thanks you so much Spirit staff!

I stopped flying spirit as much because they are crooks and thieves. It's not like other airlines where you can at least get credits they just take your money.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Uncomfortable seats and tiny tray table. Expensive snacks. Flight was on time and crew was pleasant but take me back to Southwest!

Boarding and unboarding processes were pretty smooth. I gave a low score for Boarding because of how my flight was missing from all the boards at the airport, and when I checked the flight status on the Spirit website, it said it would be departing from Terminal E, gate D15. There are no "D" gates in terminal E.

Speaker airport didn't work well, so we couldn't hear the boarding call but the plane was on time leaving and on time arriving took a while for them to open the door and there was a non-disruptive guy who was inebriated a few rows ahead of us. Overall the flight was good and we appreciate the on-time-ness

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

Everything you need to know for your flight from Chicago to Simpson Bay

Information on your arrival and departure airports