How long is the flight from Simpson Bay to Chicago?

Airlines like Spirit Airlines, Delta, and KLM fly from Simpson Bay to Chicago in about 10h 31m. The time it takes to get you to your destination can typically vary by up to 8h 55m. The distance between Simpson Bay and Chicago is about 2204 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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.

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).

Most accurate provider : When it comes to deals on Simpson Bay-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Simpson Bay-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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.

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.

$163+ Flights from Simpson Bay to Chicago

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Cheap 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 December 27, 2025.

Wed 12/313:20 pmSXM - ORD

2 stops25h 01mMultiple Airlines

Sun 1/44:44 pmORD - SXM

1 stop19h 31mMultiple Airlines

Deal found 12/26

$464

Wed 12/315:00 pmSXM - ORD

2 stops51h 53mAir Canada

Sun 1/46:00 pmORD - SXM

2 stops42h 40mAir Canada

Deal found 12/26

$519

Wed 12/314:55 pmSXM - ORD

1 stop8h 49mUnited Airlines

Sun 1/48:45 amORD - SXM

Nonstop5h 12mUnited Airlines

Deal found 12/26

$715

Best flights from Simpson Bay to Chicago
Discover carefully curated flight deals from Simpson Bay to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 27, 2025.

Sat 1/173:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Sat 1/245:32 pmORD - SXM

1 stop18h 38mSpirit Airlines

Deal found 12/26

$304

Mon 2/93:20 pmSXM - ORD

1 stop22h 02mMultiple Airlines

Mon 2/169:41 pmORD - SXM

2 stops14h 34mMultiple Airlines

Deal found 12/26

$344

Sat 1/173:43 pmSXM - ORD

1 stop29h 53mJetBlue

Sat 1/249:40 amORD - SXM

1 stop28h 41mJetBlue

Deal found 12/26

$351

Sat 1/175:00 pmSXM - ORD

2 stops20h 06mAir Canada

Sat 1/2410:35 amORD - SXM

1 stop26h 05mAir Canada

Deal found 12/26

$405

Sat 1/171:55 pmSXM - MDW

1 stop10h 12mDelta

Sat 1/246:25 amMDW - SXM

1 stop7h 38mDelta

Deal found 12/26

$552

Sat 1/173:42 pmSXM - MDW

1 stop19h 26mKLM

Sat 1/246:25 amMDW - SXM

1 stop7h 38mKLM

Deal found 12/25

$567

Mon 2/93:20 pmSXM - ORD

1 stop10h 27mSpirit Airlines

Mon 2/165:15 amORD - SXM

1 stop7h 00mSpirit Airlines

Deal found 12/26

$305

Mon 1/123:15 pmSXM - ORD

2 stops29h 10mMultiple Airlines

Wed 1/215:32 pmORD - SXM

1 stop18h 38mMultiple Airlines

Deal found 12/24

$351

Mon 1/123:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Wed 1/215:32 pmORD - SXM

1 stop18h 38mSpirit Airlines

Deal found 12/24

$333

Mon 1/121:55 pmSXM - MDW

1 stop10h 12mDelta

Wed 1/216:00 amMDW - SXM

1 stop6h 55mDelta

Deal found 12/24

$602

Mon 1/121:55 pmSXM - MDW

1 stop10h 12mKLM

Wed 1/216:00 amMDW - SXM

1 stop6h 55mKLM

Deal found 12/24

$603

Mon 1/124:20 pmSXM - MDW

1 stop19h 50mMultiple Airlines

Wed 1/216:35 pmMDW - SXM

2 stops15h 20mMultiple Airlines

Deal found 12/24

$760

Mon 2/91:55 pmSXM - MDW

1 stop10h 27mDelta

Mon 2/166:00 amMDW - SXM

1 stop6h 50mDelta

Deal found 12/26

$790

Sat 1/171:05 pmSXM - MDW

2 stops28h 15mMultiple Airlines

Sat 1/2412:45 pmMDW - SXM

2 stops23h 55mMultiple Airlines

Deal found 12/26

$929

Last-minute flights from Simpson Bay to Chicago
Discover last-minute flight deals from Simpson Bay to Chicago. Data last updated December 27, 2025 and is based on user searches.

Mon 1/123:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Wed 1/215:32 pmORD - SXM

1 stop18h 38mSpirit Airlines

Deal found 12/24

$333

Mon 1/123:15 pmSXM - ORD

2 stops29h 10mMultiple Airlines

Wed 1/215:32 pmORD - SXM

1 stop18h 38mMultiple Airlines

Deal found 12/24

$351

Mon 1/121:55 pmSXM - MDW

1 stop10h 12mDelta

Wed 1/216:00 amMDW - SXM

1 stop6h 55mDelta

Deal found 12/24

$602

Mon 1/121:55 pmSXM - MDW

1 stop10h 12mKLM

Wed 1/216:00 amMDW - SXM

1 stop6h 55mKLM

Deal found 12/24

$603

Mon 1/124:20 pmSXM - MDW

1 stop19h 50mMultiple Airlines

Wed 1/216:35 pmMDW - SXM

2 stops15h 20mMultiple Airlines

Deal found 12/24

$760

Sat 1/173:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Sat 1/245:32 pmORD - SXM

1 stop18h 38mSpirit Airlines

Deal found 12/26

$304

Sat 1/173:43 pmSXM - ORD

1 stop29h 53mJetBlue

Sat 1/249:40 amORD - SXM

1 stop28h 41mJetBlue

Deal found 12/25

$390

Sat 1/175:00 pmSXM - ORD

2 stops20h 06mAir Canada

Sat 1/2410:35 amORD - SXM

1 stop26h 05mAir Canada

Deal found 12/26

$405

Sat 1/175:00 pmSXM - ORD

1 stop18h 13mMultiple Airlines

Sat 1/247:45 amORD - SXM

2 stops28h 43mMultiple Airlines

Deal found 12/25

$411

Sat 1/175:28 pmSXM - MDW

2 stops17h 24mDelta

Sat 1/246:25 amMDW - SXM

1 stop7h 38mDelta

Deal found 12/26

$552

Sat 1/173:42 pmSXM - MDW

1 stop19h 26mKLM

Sat 1/246:25 amMDW - SXM

1 stop7h 38mKLM

Deal found 12/25

$567

Sat 1/171:05 pmSXM - MDW

2 stops28h 15mMultiple Airlines

Sat 1/2412:45 pmMDW - SXM

2 stops23h 55mMultiple Airlines

Deal found 12/26

$929

One-way flights from Simpson Bay to Chicago
Search for one-way flight options from Simpson Bay to Chicago. Find affordable one-way fares based on user searches. Data last updated December 27, 2025.

Thu 2/263:20 pmSXM - ORD

1 stop10h 27mSpirit Airlines

Deal found 12/26

$163

Wed 2/253:20 pmSXM - ORD

1 stop10h 27mSpirit Airlines

Deal found 12/26

$166

Sat 1/243:10 pmSXM - ORD

1 stop9h 34mFrontier

Deal found 12/25

$167

Fri 2/273:20 pmSXM - ORD

1 stop10h 04mMultiple Airlines

Deal found 12/26

$176

Sat 2/143:20 pmSXM - ORD

1 stop10h 27mSpirit Airlines

Deal found 12/25

$177

Mon 2/233:20 pmSXM - ORD

1 stop10h 27mSpirit Airlines

Deal found 12/26

$183

Sun 1/253:15 pmSXM - ORD

1 stop9h 34mMultiple Airlines

Deal found 12/25

$192

Mon 1/263:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/27

$201

Sun 1/253:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Deal found 12/27

$208

Fri 4/32:15 pmSXM - MDW

2 stops48h 44mMultiple Airlines

Deal found 12/27

$358

Tue 1/201:45 pmSXM - MDW

3 stops48h 00mMultiple Airlines

Deal found 12/26

$400

Tue 1/204:20 pmSXM - MDW

2 stops27h 09mWestJet

Deal found 12/26

$410

Find flight deals from Simpson Bay to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$265 (Cheapflightsfares)
One-way from	$163 (Super.com)

Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.

Search Deals

From Simpson Bay Princess Juliana to Chicago (CHI)

Search Deals

One-way flight from Simpson Bay Princess Juliana to Chicago (CHI)

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Simpson Bay to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-11:46 pm

1 stop10h 31m

Chicago O'Hare Intl

Sat 1/24

5:32 pm-2:10 pm

1 stop18h 38m

$304

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 2/9

3:20 pm-11:47 pm

1 stop10h 27m

Chicago O'Hare Intl

Mon 2/16

5:15 am-2:15 pm

1 stop7h 00m

$305

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 1/12

3:15 pm-11:22 am

1 stop22h 07m

Chicago O'Hare Intl

Wed 1/21

5:32 pm-2:10 pm

1 stop18h 38m

$333

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 2/9

3:20 pm-11:22 am

1 stop22h 02m

Chicago O'Hare Intl

Mon 2/16

9:41 pm-2:15 pm

2 stops14h 34m

$344

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

3:43 pm-7:36 pm

1 stop29h 53m

Chicago O'Hare Intl

Sat 1/24

9:40 am-4:21 pm

1 stop28h 41m

$351

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 1/12

3:15 pm-6:25 pm

2 stops29h 10m

Chicago O'Hare Intl

Wed 1/21

5:32 pm-2:10 pm

1 stop18h 38m

$351

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

5:00 pm-11:06 am

2 stops20h 06m

Chicago O'Hare Intl

Sat 1/24

10:35 am-2:40 pm

1 stop26h 05m

$405

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 1/17

1:55 pm-10:07 pm

1 stop10h 12m

Chicago Midway

Sat 1/24

6:25 am-4:03 pm

1 stop7h 38m

$552

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 1/17

3:42 pm-9:08 am

1 stop19h 26m

Chicago Midway

Sat 1/24

6:25 am-4:03 pm

1 stop7h 38m

$567

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/12

1:55 pm-10:07 pm

1 stop10h 12m

Chicago Midway

Wed 1/21

6:00 am-2:55 pm

1 stop6h 55m

$602

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 29 results

Compare providers for flights from Simpson Bay to Chicago

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 December.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*1 star
Expedia	Price Accuracy2 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Simpson Bay-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

Cheapflights Insights

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

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

When flying from Simpson Bay to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

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.
How long is the flight from Simpson Bay to Chicago?
Airlines like Spirit Airlines, Delta, and KLM fly from Simpson Bay to Chicago in about 10h 31m. The time it takes to get you to your destination can typically vary by up to 8h 55m. The distance between Simpson Bay and Chicago is about 2204 mi. Both multi-stop and nonstop flights can be found to your destination and back.
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.

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$163+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Simpson Bay to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Simpson Bay to Chicago

Cheapest flights from Simpson Bay to ChicagoExplore 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 December 27, 2025.

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 December 27, 2025.

Find flight deals from Simpson Bay to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Cheapflights Fare Finder

Use the filters below to find and compare flights from Simpson Bay to Chicago that are best for you.

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 December.

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.

Cheapflights Insights

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

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 December 27, 2025.

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?

How long is the flight from Simpson Bay to Chicago?

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

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

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

Traveling to a place near Chicago?

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Alternative routes for Simpson Bay to Chicago

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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 December 27, 2025.