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$209 Find Cheap Flights from Simpson Bay to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Simpson Bay to Illinois departing on 4/25. 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.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Illinois, 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 Simpson Bay to Illinois, as well as popular online travel agencies
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Best Illinois Flight Deals from Simpson Bay

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicago1 stop$478

Cheap Flight Deals from Simpson Bay to Illinois (SXM-USIL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Simpson Bay to Illinois 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.

Recent round-trip flight deals from Simpson Bay to Illinois

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Simpson Bay to Illinois.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:05 pm - 12:58 amSXM-ORD
10h 53m1 stop
5:36 am - 2:00 pmORD-SXM
7h 24m1 stop
$478Spirit Airlines
Find Deal
Sat, Apr 19 - Fri, Apr 25
12:05 pm - 8:55 amSXM-ORD
21h 50m2 stops
5:36 am - 2:00 pmORD-SXM
7h 24m1 stop
$492
Find Deal
Thu, Apr 3 - Wed, Apr 9
12:05 pm - 12:03 pmSXM-ORD
24h 58m3 stops
5:36 am - 2:00 pmORD-SXM
7h 24m1 stop
$508
Find Deal
Thu, Apr 3 - Wed, Apr 9
1:40 pm - 10:21 pmSXM-MDW
9h 41m1 stop
6:00 am - 1:59 pmMDW-SXM
6h 59m1 stop
$613Delta
Find Deal
Thu, Apr 3 - Wed, Apr 9
4:15 pm - 12:20 amSXM-ORD
9h 05m1 stop
5:10 am - 3:24 pmORD-SXM
9h 14m2 stops
$623American Airlines
Find Deal
Thu, Apr 3 - Wed, Apr 9
4:05 pm - 9:05 amSXM-ORD
18h 00m1 stop
6:55 pm - 3:05 pmORD-SXM
19h 10m1 stop
$628American Airlines
Find Deal
Wed, Jun 11 - Sun, Jun 15
4:05 pm - 9:25 amSXM-ORD
18h 20m2 stops
6:55 pm - 3:05 pmORD-SXM
19h 10m1 stop
$755British Airways
Find Deal
Wed, Jun 11 - Sun, Jun 15
1:25 pm - 6:08 pmSXM-ORD
5h 43mnonstop
10:37 am - 4:49 pmORD-SXM
5h 12mnonstop
$850Lufthansa
Find Deal
Sat, Apr 19 - Sat, Apr 26
1:25 pm - 6:08 pmSXM-ORD
5h 43mnonstop
6:20 pm - 12:29 pmORD-SXM
17h 09m1 stop
$932Lufthansa
Find Deal
Sat, Apr 19 - Sat, Apr 26
1:46 pm - 10:22 pmSXM-MDW
9h 36m1 stop
6:45 pm - 2:05 pmMDW-SXM
18h 20m1 stop
$1,341Delta
Find Deal
Sat, Apr 19 - Sat, Apr 26

Good to know

Low season

February

High season

October

Cheapest flight

$209
Best time to beat the crowds with an average 46% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Simpson Bay to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How long is the flight to Illinois from Simpson Bay?

    Flights to Chicago5h 27m

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

    The cheapest ticket to Illinois from Simpson Bay found in the last 72 hours was $209 one-way, and $478 round-trip. The most popular route is from Simpson Bay Princess Juliana to Chicago O'Hare Intl, and the cheapest round-trip airline ticket found on this route in the last 72 hours was $209.

  • Which airlines fly to Illinois?

    United Airlines flies most frequently to Chicago O'Hare Intl from Simpson Bay Princess Juliana.

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

    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 Simpson Bay to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Simpson Bay to Illinois 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 Simpson Bay to Illinois?

    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 from Simpson Bay to Illinois with an airline and back with another airline.

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

    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 from Simpson Bay to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Illinois

  • High season is considered to be March, April and May. The cheapest month to fly from Simpson Bay is February.
  • Morning departure is around 171% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top airline flying from Simpson Bay to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Simpson Bay to Illinois. 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 Simpson Bay to Illinois? 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.
7.2
American AirlinesOverall score based on 10000 reviews
7.3Comfort
6.5Food
7.5Boarding
7.0Entertainment
8.0Crew
Airline reviews

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

10.0 ExcellentDr. Joseph, Feb 2025DCA - ORD
Read more American Airlines reviews

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

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

Information on your arrival and departure airports

Simpson Bay (SXM)

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