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Cheap flights from Chicago (CHI) to Simpson Bay (SXM) from $60

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/17. 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.
CHI — SXM
May 12 — May 191
From?
To?
Sun 5/12
Sun 5/19
1 adult, Economy
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The best prices from Chicago to Simpson Bay Princess Juliana are usually found in September or January, booked 54 days in advance, depart on a Wednesday or Monday and return on a Monday

Cheap flight deals from Chicago to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 7, 2024.

Popular in

July

Cheapest in

September

Round-trip from

$535

One-way from

$60
High demand for flights, 21% potential price rise
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Best time to find cheap flights, 13% potential price drop
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From Chicago (CHI) to Simpson Bay Princess Juliana
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One-way flight from Chicago (CHI) to Simpson Bay Princess Juliana
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What is the cheapest day to fly round-trip from Chicago to Simpson Bay?

Departing on a Tuesday is a good option for securing a great price. You can expect to save up to 32% when planning your travel around this day of the week.

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

Travelers have found it’s best to book a flight 55 days in advance to save up to 550% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 55 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Simpson Bay 1-2 weeks in advance for as low as $464, or $841 for flights within the next 24 hours.

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

Flights from Chicago to Simpson Bay lean towards being more expensive in July. Prices are generally better when you fly from Chicago to Simpson Bay in September, with the cheapest ticket starting at $481.

When is the cheapest time to fly from Chicago to Simpson Bay (CHI - SXM)?

When flying from Chicago to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 46% versus a flight in the morning.

Cheap Frontier flights from Chicago to Simpson Bay

Explore cheap flight options specifically provided by Frontier for the route between Chicago and Simpson Bay. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Peruse some of the lowest-priced Frontier flights we've found from Chicago to Simpson Bay. Make sure to check back often as deals are often changing.
Fri 5/175:56 pmORD - SXM
1 stop20h 08mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$189
Sat 5/185:56 pmORD - SXM
1 stop20h 11mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$244
Sat 5/1811:00 amORD - SXM
2 stops27h 07mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$288
Sat 6/111:05 amORD - SXM
2 stops26h 59mFrontier
Sat 6/84:20 pmSXM - ORD
1 stop27h 45mFrontier
Deal found 5/6$294
Thu 6/68:51 pmMDW - SXM
2 stops19h 24mFrontier
Fri 6/146:25 pmSXM - MDW
2 stops15h 09mFrontier
Deal found 5/6$299
Thu 6/68:51 pmMDW - SXM
2 stops19h 24mFrontier
Mon 6/106:25 pmSXM - MDW
2 stops38h 06mFrontier
Deal found 5/6$301
Fri 5/176:50 pmORD - SXM
2 stops19h 14mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$428
Fri 5/176:50 pmORD - SXM
2 stops19h 14mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$429

Cheap Spirit Airlines flights from Chicago to Simpson Bay

Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Simpson Bay. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Have a look at some of the cheapest available Spirit Airlines flights departing from Chicago and landing in Simpson Bay. Make sure to examine the flight information before completing your reservation.
Wed 6/55:05 amORD - SXM
1 stop7h 43mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$260
Wed 6/55:05 amORD - SXM
1 stop7h 43mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$263
Tue 6/46:40 pmORD - SXM
1 stop18h 08mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$271
Thu 5/306:40 pmORD - SXM
1 stop18h 04mSpirit Airlines
Mon 6/32:44 pmSXM - ORD
1 stop9h 45mSpirit Airlines
Deal found 5/6$299
Mon 6/35:00 amORD - SXM
1 stop7h 44mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$303
Wed 5/295:00 amORD - SXM
1 stop7h 44mSpirit Airlines
Fri 6/72:44 pmSXM - ORD
1 stop11h 11mSpirit Airlines
Deal found 5/6$304
Wed 6/55:05 amORD - SXM
1 stop7h 43mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
2 stops22h 16mSpirit Airlines
Deal found 5/6$312
Sun 6/25:41 pmORD - SXM
1 stop19h 03mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$317
Sun 6/96:40 pmORD - SXM
1 stop18h 08mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$319

Cheap Chicago to Simpson Bay flights in May & June 2024

Find cheap flight options from Chicago to Simpson Bay specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Prices were last updated on May 7, 2024.
These are some of the best deals we've found on flights to Simpson Bay in 2024 at this time. Check back soon for alternative fares.
Fri 5/175:56 pmORD - SXM
1 stop20h 08mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$189
Sat 5/185:56 pmORD - SXM
1 stop20h 11mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$244
Wed 6/55:05 amORD - SXM
1 stop7h 43mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$260
Wed 6/55:05 amORD - SXM
1 stop7h 43mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$263
Tue 6/46:40 pmORD - SXM
1 stop18h 08mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$271
Sat 5/1811:00 amORD - SXM
2 stops27h 07mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$288
Sat 5/185:56 pmORD - SXM
1 stop20h 11mMultiple Airlines
Wed 5/222:44 pmSXM - ORD
1 stop27h 56mMultiple Airlines
Deal found 5/7$291
Sat 6/111:05 amORD - SXM
2 stops26h 59mFrontier
Sat 6/84:20 pmSXM - ORD
1 stop27h 45mFrontier
Deal found 5/6$294
Thu 6/68:51 pmMDW - SXM
2 stops19h 24mFrontier
Fri 6/146:25 pmSXM - MDW
2 stops15h 09mFrontier
Deal found 5/6$299

Chicago to Simpson Bay 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Simpson Bay in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
These are some of the best deals we've found on flights to Simpson Bay in 2024 at this time. Check back soon for alternative fares.
Fri 5/175:56 pmORD - SXM
1 stop20h 08mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$189
Sat 5/185:56 pmORD - SXM
1 stop20h 11mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$244
Wed 6/55:05 amORD - SXM
1 stop7h 43mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$260
Wed 6/55:05 amORD - SXM
1 stop7h 43mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$263
Tue 6/46:40 pmORD - SXM
1 stop18h 08mSpirit Airlines
Wed 6/122:44 pmSXM - ORD
1 stop9h 09mSpirit Airlines
Deal found 5/6$271
Sat 5/1811:00 amORD - SXM
2 stops27h 07mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$288
Sat 5/185:56 pmORD - SXM
1 stop20h 11mMultiple Airlines
Wed 5/222:44 pmSXM - ORD
1 stop27h 56mMultiple Airlines
Deal found 5/7$291
Sat 6/111:05 amORD - SXM
2 stops26h 59mFrontier
Sat 6/84:20 pmSXM - ORD
1 stop27h 45mFrontier
Deal found 5/6$294
Thu 6/68:51 pmMDW - SXM
2 stops19h 24mFrontier
Fri 6/146:25 pmSXM - MDW
2 stops15h 09mFrontier
Deal found 5/6$299

Non-stop flights to Simpson Bay from Chicago

Discover non-stop flight options from Chicago to Simpson Bay. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Take a look at some of the direct flights traveling from Chicago to Simpson Bay in the near future. If you're looking for other options for flights from Chicago to Simpson Bay, make sure to update the search form at the top of page.
Sat 6/810:43 amORD - SXM
Nonstop5h 06mUnited Airlines
Sat 6/151:30 pmSXM - ORD
Nonstop5h 44mUnited Airlines
Deal found 5/6$680
Sat 7/610:43 amORD - SXM
Nonstop5h 06mUnited Airlines
Sat 7/131:30 pmSXM - ORD
Nonstop5h 44mUnited Airlines
Deal found 5/7$690
Sat 7/2710:43 amORD - SXM
Nonstop5h 06mUnited Airlines
Sat 8/31:30 pmSXM - ORD
Nonstop5h 44mUnited Airlines
Deal found 5/7$720
Sat 6/110:43 amORD - SXM
Nonstop5h 06mUnited Airlines
Sat 6/81:30 pmSXM - ORD
Nonstop5h 44mUnited Airlines
Deal found 5/6$765
Sat 6/2910:43 amORD - SXM
Nonstop5h 06mUnited Airlines
Sat 7/61:30 pmSXM - ORD
Nonstop5h 44mUnited Airlines
Deal found 5/6$920
Sat 6/2210:43 amORD - SXM
Nonstop5h 06mUnited Airlines
Sat 6/291:30 pmSXM - ORD
Nonstop5h 44mUnited Airlines
Deal found 5/7$983
Sat 11/28:51 amORD - SXM
Nonstop5h 00mUnited Airlines
Sat 11/92:55 pmSXM - ORD
Nonstop5h 50mUnited Airlines
Deal found 5/6$1,391

Chicago to Simpson Bay flights leaving soon

Find last-minute flight options from Chicago to Simpson Bay for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Users seeking a last-minute flight from Chicago to Simpson Bay should consider booking one of these fares. Users should be sure to double check the price, date, and time of their last-minute flight.
Fri 5/175:56 pmORD - SXM
1 stop20h 08mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$189
Tue 5/146:40 pmORD - SXM
1 stop18h 04mSpirit Airlines
Mon 5/202:44 pmSXM - ORD
3 stops26h 14mSpirit Airlines
Deal found 5/6$343
Tue 5/146:40 pmORD - SXM
1 stop18h 04mSpirit Airlines
Mon 5/202:44 pmSXM - ORD
1 stop9h 45mSpirit Airlines
Deal found 5/6$348
Tue 5/149:25 pmORD - SXM
2 stops15h 19mSpirit Airlines
Mon 5/202:44 pmSXM - ORD
3 stops26h 14mSpirit Airlines
Deal found 5/6$365
Tue 5/145:36 pmORD - SXM
3 stops19h 08mSpirit Airlines
Mon 5/202:44 pmSXM - ORD
3 stops26h 14mSpirit Airlines
Deal found 5/6$379
Tue 5/149:25 pmORD - SXM
2 stops15h 19mSpirit Airlines
Mon 5/202:44 pmSXM - ORD
1 stop9h 45mSpirit Airlines
Deal found 5/6$380
Fri 5/177:35 amORD - SXM
3 stops29h 09mSpirit Airlines
Sat 5/252:44 pmSXM - ORD
1 stop9h 45mSpirit Airlines
Deal found 5/6$422
Fri 5/177:35 amORD - SXM
3 stops29h 09mSpirit Airlines
Sat 5/252:44 pmSXM - ORD
1 stop9h 45mSpirit Airlines
Deal found 5/6$424
Fri 5/176:50 pmORD - SXM
2 stops19h 14mFrontier
Sat 5/254:14 pmSXM - ORD
1 stop9h 44mFrontier
Deal found 5/6$428

One-way flights to Simpson Bay from Chicago

Search for one-way flight options from Chicago to Simpson Bay. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Take a look at some of the best available options we've come across on one-way flights from Chicago to Simpson Bay. Users can also find round-trip Chicago to Simpson Bay flights by using the search form above.
Fri 5/175:56 pmORD - SXM
1 stop20h 08mFrontier
Deal found 5/6$60
Thu 5/306:40 pmORD - SXM
1 stop18h 04mSpirit Airlines
Deal found 5/6$118
Thu 5/306:21 pmORD - SXM
2 stops18h 23mSpirit Airlines
Deal found 5/6$157
Thu 5/166:40 pmORD - SXM
1 stop18h 04mSpirit Airlines
Deal found 5/7$166
Thu 5/306:12 amORD - SXM
3 stops30h 32mSpirit Airlines
Deal found 5/6$180
Fri 5/175:23 pmORD - SXM
2 stops19h 21mSpirit Airlines
Deal found 5/6$191
Fri 5/177:35 amORD - SXM
3 stops29h 09mSpirit Airlines
Deal found 5/6$192
Thu 5/165:36 pmORD - SXM
2 stops19h 08mSpirit Airlines
Deal found 5/7$223
Thu 5/166:12 amORD - SXM
3 stops30h 32mSpirit Airlines
Deal found 5/7$279

Find flights from Chicago to Simpson Bay within your budget

Customize your flight search to find flights from Chicago to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$189 - $555

Route

Depart

Return

Price

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/17

1 stop20h 08m

Simpson Bay Princess Juliana

Sat 5/25

1 stop9h 44m

$189

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/18

1 stop20h 11m

Simpson Bay Princess Juliana

Sat 5/25

1 stop9h 44m

$244

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 6/5

1 stop7h 43m

Simpson Bay Princess Juliana

Wed 6/12

1 stop9h 09m

$260

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 6/5

1 stop7h 43m

Simpson Bay Princess Juliana

Wed 6/12

1 stop9h 09m

$263

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 6/4

1 stop18h 08m

Simpson Bay Princess Juliana

Wed 6/12

1 stop9h 09m

$271

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/18

1 stop20h 11m

Simpson Bay Princess Juliana

Wed 5/22

1 stop27h 56m

$291

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/1

1 stop7h 44m

Simpson Bay Princess Juliana

Sat 6/8

1 stop27h 45m

$300

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/26

1 stop15h 40m

Simpson Bay Princess Juliana

Fri 11/8

1 stop18h 03m

$553

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 6/3

1 stop7h 00m

Simpson Bay Princess Juliana

Thu 6/13

1 stop9h 36m

$555

Flights are sorted by cheapest first

Deals found on 5/6

When is the best time to book a flight from Chicago to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Simpson Bay. Price data was last updated on May 3, 2024.
The price you pay for your flight from Chicago to Simpson Bay may vary depending on when you book. For the best chance of a lower fare, look to book 54 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

When is the cheapest time to fly from Chicago to Simpson Bay?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Simpson Bay. Price data was last updated on May 5, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Simpson Bay flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Simpson Bay by month

Plan your trip from Chicago to Simpson Bay by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Simpson Bay is currently $174 while a round-trip flight costs $325. Price data was last updated on May 5, 2024.

Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $535). Flying from Chicago to Simpson Bay in July is currently the most expensive (average of $777). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$548

February

$588

March

$656

April

$605

May

$580

June

$660

July

$777

August

$648

September

$535

October

$656

November

$603

December

$633

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated May 7, 2024.
Get a feel of what it's like to fly with Frontier, Spirit Airlines and American Airlines from Chicago to Simpson Bay by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,810 reviews
Check prices

Crew

8.6

Comfort

7.9

Overall

8.1

Entertainment

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.1
Very good
10,810 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Crew

8.6

Comfort

7.9

Overall

8.1

Entertainment

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

United Airlines
7.4
Good
11,073 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Crew

8.6

Comfort

7.9

Overall

8.1

Entertainment

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

American Airlines
7.3
Good
14,686 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Crew

8.6

Comfort

7.9

Overall

8.1

Entertainment

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Spirit Airlines
6.4
Okay
8,711 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Crew

8.6

Comfort

7.9

Overall

8.1

Entertainment

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,088 reviews
Delta
8.1
Very good
10,810 reviews
Check prices

Crew

8.6

Comfort

7.9

Overall

8.1

Entertainment

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Simpson Bay from Chicago?

    Most people fly into Simpson Bay Princess Juliana (SXM) if they book a flight to Simpson Bay from Chicago. On average, Princess Juliana has 0 inbound flights from Chicago per day from 4 airlines. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

  • Can I find flights from Chicago to Simpson Bay for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Simpson Bay for under $200. The cheapest flight booked recently is on Frontier for just $189, but on average you can expect to pay $291.

  • Are there nonstop flights from Chicago to Simpson Bay for under $700 on Cheapflights?

    Cheapflights has at least 7 direct flights from Chicago to Simpson Bay under $700. A good price for a nonstop flight from Chicago to Simpson Bay is less than $878.

  • Are there last-minute flights available from Chicago to Simpson Bay for under $200?

    There are currently 20+ open flights from Chicago to Simpson Bay within the next 7 days for less than $200.

  • What are the cheapest airlines flying from Chicago to Simpson Bay round-trip?

    According to our current data, Frontier ($189), and Spirit Airlines ($260) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Frontier is 74% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Simpson Bay one-way?

    $60 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and American Airlines, with prices starting from $118 and $283, respectively.

  • What are the most popular airlines that fly from Chicago to Simpson Bay?

    Consider American Airlines, Delta or Spirit Airlines when booking your flight. These represent the most popular airlines when flying from Chicago to Simpson Bay.

  • What are the cheapest flights from Chicago to Simpson Bay?

    On average you can expect to pay $626 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $297 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $260.

  • What does ORD to SXM mean?

    Chicago O'Hare Intl Airport is ORD and Simpson Bay Princess Juliana Airport is SXM. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Simpson Bay that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Simpson Bay flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Simpson Bay with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Simpson Bay flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Chicago to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Simpson Bay.

  • Can I find deals for business class flights from Chicago to Simpson Bay?

    Yes. Cheapflights offers flight deals from Chicago to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Simpson Bay that allow pets onboard?

    Many airlines flying from Chicago to Simpson Bay offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Simpson Bay?

    Yes, you can often find last-minute deals on Chicago to Simpson Bay flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Simpson Bay flight deals updated?

    The Chicago to Simpson Bay flight deals you see on this page were last updated on 5/7.

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Alternative routes for Chicago to Simpson Bay
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Top 4 airlines flying from Chicago to Simpson Bay

Discover the top 4 airlines that operate flights from Chicago to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$267Average$577FlexibilityNo cancel feeOn-time65%
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United AirlinesCheapest$441Average$895FlexibilityNo cancel feeOn-time69%
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DeltaCheapest$473Average$827FlexibilityNo cancel feeOn-timeN/A
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American AirlinesCheapest$551Average$762FlexibilityNo cancel feeOn-time71%
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Search flights from Chicago to Simpson Bay by cabin class

Find flights from Chicago to Simpson Bay, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Weekly flight availability from Chicago to Simpson Bay

Explore weekly flight availability from Chicago to Simpson Bay. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 7, 2024.
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Why should you use Cheapflights to find cheap flight tickets from Chicago to Simpson Bay?

Cheapflights simply makes it quick and affordable to book flights from Chicago to Simpson Bay by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Chicago to Simpson Bay with no change fees?

Need flexible booking options for your flight to Simpson Bay from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Simpson Bay become cheaper?

Of course! You can now track prices for flights from Chicago to Simpson Bay and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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