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$178+ Cheap flights from Simpson Bay (SXM) to Chicago (CHI)

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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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Cheap flight deals from Simpson Bay to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Simpson Bay (SXM) to Chicago (CHI). 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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$362
(Booking.com)

One-way from

$178
(Kiwi.com)

Popular in

April

Cheapest in

February

Average price

$338

Good one-way deal

$459 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
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From Simpson Bay Princess Juliana to Chicago (CHI)
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One-way flight from Simpson Bay Princess Juliana to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Chicago (CHI).
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Find flight deals from Simpson Bay to Chicago

Cheapest flights from Simpson Bay to Chicago
Explore the most affordable flight options available from Simpson Bay to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This Booking.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/302:34 pmSXM - ORD
1 stop11h 07mSpirit Airlines
vie. 5/95:05 amORD - SXM
1 stop7h 56mSpirit Airlines
Deal found 2/18$362
This Kiwi.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/302:34 pmSXM - ORD
1 stop11h 07mMultiple Airlines
vie. 5/94:15 pmORD - SXM
2 stops18h 05mMultiple Airlines
Deal found 2/18$421
This eDestinos deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/1212:18 pmSXM - ORD
2 stops24h 14mFrontier
vie. 8/16:00 amORD - SXM
2 stops27h 58mFrontier
Deal found 2/19$555
This American Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/292:14 pmSXM - ORD
2 stops10h 35mAmerican Airlines
vie. 5/95:00 amORD - SXM
2 stops9h 31mAmerican Airlines
Deal found 2/18$662
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/303:55 pmSXM - MDW
2 stops25h 45mMultiple Airlines
lun. 4/75:35 pmMDW - SXM
1 stop19h 41mMultiple Airlines
Deal found 2/20$781
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/191:25 pmSXM - ORD
Nonstop5h 43mUnited Airlines
vie. 4/254:15 pmORD - SXM
1 stop19h 14mUnited Airlines
Deal found 2/20$806
This Flysmarter deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/91:16 pmSXM - ORD
Nonstop5h 54mLufthansa
dom. 3/167:40 pmORD - SXM
1 stop16h 11mLufthansa
Deal found 2/20$861
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/91:40 pmSXM - MDW
1 stop9h 43mDelta
dom. 3/164:59 pmMDW - SXM
1 stop20h 02mDelta
Deal found 2/20$1,016
This WestJet deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/112:10 pmSXM - ORD
2 stops27h 34mWestJet
sáb. 5/175:30 pmORD - SXM
2 stops18h 45mWestJet
Deal found 2/20$1,138
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/303:10 pmSXM - MDW
2 stops28h 08mWestJet
lun. 4/71:15 pmMDW - SXM
2 stops24h 01mWestJet
Deal found 2/20$1,202
This Gotogate deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/93:55 pmSXM - ORD
2 stops28h 43mAir Canada
dom. 3/169:40 pmORD - SXM
2 stops16h 35mAir Canada
Deal found 2/20$1,754

Find flights from Simpson Bay to Chicago within your budget

Customize your flight search to find flights from Simpson Bay to Chicago 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 2,558,603 searches. Data last updated febrero 20, 2025.

Fly from

Simpson Bay

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

mié. 4/30

2:34 pm-12:41 am

1 stop11h 07m

Chicago O'Hare Intl

vie. 5/9

5:05 am-2:01 pm

1 stop7h 56m

$362

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

mié. 4/30

2:34 pm-12:41 am

1 stop11h 07m

Chicago O'Hare Intl

vie. 5/9

4:15 pm-11:20 am

2 stops18h 05m

$421

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 7/12

12:18 pm-11:32 am

2 stops24h 14m

Chicago O'Hare Intl

vie. 8/1

6:00 am-10:58 am

2 stops27h 58m

$555

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

mar. 4/29

2:14 pm-11:49 pm

2 stops10h 35m

Chicago O'Hare Intl

vie. 5/9

5:00 am-3:31 pm

2 stops9h 31m

$662

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

dom. 3/30

3:55 pm-4:40 pm

2 stops25h 45m

Chicago Midway

lun. 4/7

5:35 pm-2:16 pm

1 stop19h 41m

$781

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 4/19

1:25 pm-6:08 pm

Nonstop5h 43m

Chicago O'Hare Intl

vie. 4/25

4:15 pm-12:29 pm

1 stop19h 14m

$806

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

dom. 3/9

1:16 pm-6:10 pm

Nonstop5h 54m

Chicago O'Hare Intl

dom. 3/16

7:40 pm-12:51 pm

1 stop16h 11m

$861

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

dom. 3/9

1:40 pm-10:23 pm

1 stop9h 43m

Chicago Midway

dom. 3/16

4:59 pm-2:01 pm

1 stop20h 02m

$1,016

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

dom. 5/11

2:10 pm-4:44 pm

2 stops27h 34m

Chicago O'Hare Intl

sáb. 5/17

5:30 pm-1:15 pm

2 stops18h 45m

$1,138

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

dom. 3/30

3:10 pm-6:18 pm

2 stops28h 08m

Chicago Midway

lun. 4/7

1:15 pm-2:16 pm

2 stops24h 01m

$1,202

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 20 results
1
2

Compare providers for flights from Simpson Bay to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Simpson Bay to Chicago in February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Simpson Bay-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Simpson Bay-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Simpson Bay-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Simpson Bay-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Simpson Bay-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Simpson Bay to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Simpson Bay with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Simpson Bay to Chicago

Get recent, data-driven insights about flights from Simpson Bay to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest time of day to fly from SXM to CHI?

Find hourly flight availability from Simpson Bay to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Simpson Bay to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated febrero 20, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines and American Airlines from Simpson Bay to Chicago to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,765 reviews
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.2
Good
2,801 reviews
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Canada
7.0
Good
8,748 reviews
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Chicago. 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 from for flights from Simpson Bay to Chicago?

    Most people fly from Simpson Bay Princess Juliana (SXM) if they book a flight from Simpson Bay to Chicago. On average, Princess Juliana has 0 outbound flights to Chicago per day from 1 airline. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

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

    According to our current data, Spirit Airlines ($362), Frontier ($555), and American Airlines ($662) offers the cheapest pricing from Simpson Bay to Chicago. Spirit Airlines is 41% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Simpson Bay to Chicago are Spirit Airlines ($239), Air Canada ($375), and American Airlines ($390).

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

    On average you can expect to pay $809 for a flight from Simpson Bay to Chicago. The cheapest flight overall is $446 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $362.

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

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Simpson Bay to Chicago (average of $245). Flying from Simpson Bay to Chicago in March is currently the most expensive (average of $321). 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.

See more FAQs

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Simpson Bay to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Simpson Bay to O'Hare Intl flights
Simpson Bay to Midway flights

Top airline flying from Simpson Bay to Chicago

Discover the top airline that operate flights from Simpson Bay to Chicago. 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 2,558,603 searches. Data last updated febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%
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