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$317+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$640
(Frontier)

One-way from

$317
(Cheapflightsfares)

Popular in

January

Cheapest in

February

Average price

$1,086

Good one-way deal

$687 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. 0% potential increase in price ($0 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 21, 2025.

This Frontier deal was found by Cheapflights users on 1/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1212:18 pmSXM - ORD
1 stop12h 20mFrontier
Fri 8/16:01 pmORD - SXM
2 stops15h 57mFrontier
Deal found 1/21$640
This SmartFares deal was found by Cheapflights users on 1/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1212:18 pmSXM - MDW
1 stop8h 41mFrontier
Fri 8/19:12 pmMDW - SXM
1 stop12h 46mFrontier
Deal found 1/21$660
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/174:15 pmSXM - ORD
1 stop8h 36mAmerican Airlines
Tue 7/226:59 amORD - SXM
1 stop7h 16mAmerican Airlines
Deal found 1/20$680
This Justfly.com deal was found by Cheapflights users on 1/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/194:45 pmSXM - ORD
1 stop18h 16mAir Canada
Fri 4/258:25 pmORD - SXM
1 stop18h 20mAir Canada
Deal found 1/21$701
This WestJet deal was found by Cheapflights users on 1/20. 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.
Thu 7/172:10 pmSXM - ORD
2 stops47h 29mWestJet
Tue 7/225:30 pmORD - SXM
2 stops42h 45mWestJet
Deal found 1/20$987
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Sat 4/191:25 pmSXM - ORD
Nonstop5h 43mUnited Airlines
Fri 4/259:05 pmORD - SXM
1 stop14h 24mUnited Airlines
Deal found 1/21$1,172
This Orbitz deal was found by Cheapflights users on 1/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/126:10 pmSXM - ORD
2 stops43h 44mMultiple Airlines
Fri 8/110:00 amORD - SXM
2 stops22h 25mMultiple Airlines
Deal found 1/21$4,209

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/12

12:18 pm-11:38 pm

1 stop12h 20m

Chicago O'Hare Intl

Fri 8/1

6:01 pm-10:58 am

2 stops15h 57m

$640

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 7/12

12:18 pm-7:59 pm

1 stop8h 41m

Chicago Midway

Fri 8/1

9:12 pm-10:58 am

1 stop12h 46m

$660

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 7/17

4:15 pm-11:51 pm

1 stop8h 36m

Chicago O'Hare Intl

Tue 7/22

6:59 am-3:15 pm

1 stop7h 16m

$680

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/19

4:45 pm-10:01 am

1 stop18h 16m

Chicago O'Hare Intl

Fri 4/25

8:25 pm-3:45 pm

1 stop18h 20m

$701

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 7/17

2:10 pm-12:39 pm

2 stops47h 29m

Chicago O'Hare Intl

Tue 7/22

5:30 pm-1:15 pm

2 stops42h 45m

$987

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/19

1:25 pm-6:08 pm

Nonstop5h 43m

Chicago O'Hare Intl

Fri 4/25

9:05 pm-12:29 pm

1 stop14h 24m

$1,172

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/12

6:10 pm-12:54 pm

2 stops43h 44m

Chicago O'Hare Intl

Fri 8/1

10:00 am-9:25 am

2 stops22h 25m

$4,209

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 1/27

3:25 pm-11:32 pm

1 stop10h 07m

$317

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 3/30

3:55 pm-6:54 pm

2 stops27h 59m

$364

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 4/25

12:18 pm-12:32 am

1 stop13h 14m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 16 results
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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 January.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
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 January 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Simpson Bay to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 19% on your trip compared to booking a flight in the morning.

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 January 21, 2025.
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

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

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

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

Copa Airlines
7.7
Good
1,662 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

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

United Airlines
7.4
Good
8,985 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

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
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

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

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

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 0 airlines. 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, Frontier ($640), American Airlines ($680), and Air Canada ($701) offers the cheapest pricing from Simpson Bay to Chicago. Frontier is 11% 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 ($317), Air Canada ($364), and Copa Airlines ($381).

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

    On average you can expect to pay $1,615 for a flight from Simpson Bay to Chicago. The cheapest flight overall is $638 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $575.

  • 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 $320). 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

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Alternative routes for Simpson Bay to Chicago

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