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$208+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$567
(Mytrip)

One-way from

$208
(SmartFares)
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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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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/12. 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.
Sun 7/278:35 pmSXM - ORD
3 stops35h 29mMultiple Airlines
Sun 8/311:11 amORD - SXM
2 stops25h 49mMultiple Airlines
Deal found 6/12$567
This American Airlines deal was found by Cheapflights users on 6/11. 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 10/94:10 pmSXM - ORD
1 stop8h 47mAmerican Airlines
Wed 10/156:57 amORD - SXM
1 stop7h 13mAmerican Airlines
Deal found 6/11$588
This Copa Airlines deal was found by Cheapflights users on 6/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2712:23 pmSXM - ORD
1 stop12h 57mCopa Airlines
Sat 8/21:07 amORD - SXM
1 stop9h 17mCopa Airlines
Deal found 6/12$1,390

Cheapflights Fare Finder

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 June 12, 2025.
Use the filters below to find and compare flights from Simpson Bay to Chicago that are best for you.

Fly from

Simpson Bay

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 7/27

8:35 pm-7:04 am

3 stops35h 29m

Chicago O'Hare Intl

Sun 8/3

11:11 am-2:00 pm

2 stops25h 49m

$567

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:10 pm-11:57 pm

1 stop8h 47m

Chicago O'Hare Intl

Wed 10/15

6:57 am-3:10 pm

1 stop7h 13m

$588

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 7/27

12:23 pm-12:20 am

1 stop12h 57m

Chicago O'Hare Intl

Sat 8/2

1:07 am-11:24 am

1 stop9h 17m

$1,390

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/12

3:05 pm-11:53 pm

1 stop9h 48m

$208

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 6/21

12:36 pm-8:17 pm

1 stop8h 41m

$284

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/21

12:36 pm-7:09 am

1 stop19h 33m

$289

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 6/22

8:35 pm-6:37 am

2 stops35h 02m

$331

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 6/22

2:10 pm-8:45 am

1 stop19h 35m

$357

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/26

2:34 pm-10:29 pm

1 stop8h 55m

$465

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 6/22

2:10 pm-9:41 am

2 stops44h 31m

$526

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 11 results
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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

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 June 12, 2025.
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,451 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,052 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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, American Airlines ($588), and Copa Airlines ($1,390) offers the cheapest pricing from Simpson Bay to Chicago.

  • 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 ($208), Frontier ($284), and American Airlines ($465).

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%

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