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Cheap flights from Simpson Bay (SXM) to Chicago (CHI) from $172

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 9/4. 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.
SXM — CHI
Jun 2 — Jun 91
From?
To?
Sun 6/2
Sun 6/9
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 May 28, 2024.

Popular in

January

Cheapest in

November

Average price

$579

Round-trip from

$222
High demand for flights, 36% potential price rise
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Best time to find cheap flights, 61% potential price drop
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Average for round-trip flights in May 2024
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From Simpson Bay Princess Juliana to Chicago (CHI)
Search Deals

What is the cheapest day to fly round-trip from Simpson Bay to Chicago?

Leaving on a Tuesday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 30% on the overall cost on flights from Simpson Bay to Chicago.

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

Due to multiple factors, expect to potentially pay more when booking in January. For low rates, November can be a great choice for travel to Chicago. Flights to Chicago from Simpson Bay in November are about $699 on average during November, but can be found for as low as $214.

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

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 28% on your trip compared to booking a flight in the morning.

Cheap Spirit Airlines flights from Simpson Bay to Chicago

Explore cheap flight options specifically provided by Spirit Airlines for the route between Simpson Bay and Chicago. 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 2,740,132 searches. Data last updated May 28, 2024.
Take a peek at the cheapest Spirit Airlines flights we've detected traveling from Simpson Bay to Chicago. It's recommended that users confirm their flight details before booking.
Wed 7/103:05 pmSXM - ORD
1 stop19h 18mSpirit Airlines
Wed 7/175:00 amORD - SXM
1 stop8h 05mSpirit Airlines
Deal found 5/27$326
Wed 7/103:05 pmSXM - ORD
2 stops21h 55mSpirit Airlines
Wed 7/175:00 amORD - SXM
1 stop8h 05mSpirit Airlines
Deal found 5/27$331
Wed 7/103:05 pmSXM - ORD
2 stops25h 05mSpirit Airlines
Wed 7/1710:24 amORD - SXM
2 stops50h 41mSpirit Airlines
Deal found 5/27$475

Cheap American Airlines flights from Simpson Bay to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Simpson Bay and Chicago. 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 2,740,132 searches. Data last updated May 28, 2024.
To aid your search, here are some of the cheapest American Airlines flights we've found from Simpson Bay to Chicago. Deals frequently update to provide users with more options.
Fri 11/85:00 pmSXM - ORD
2 stops16h 37mAmerican Airlines
Mon 11/116:55 amORD - SXM
1 stop7h 07mAmerican Airlines
Deal found 5/27$547
Fri 11/83:39 pmSXM - ORD
1 stop22h 33mAmerican Airlines
Mon 11/115:29 amORD - SXM
1 stop6h 31mAmerican Airlines
Deal found 5/27$553
Fri 11/85:00 pmSXM - ORD
2 stops16h 37mAmerican Airlines
Mon 11/115:29 amORD - SXM
2 stops8h 33mAmerican Airlines
Deal found 5/27$587

Simpson Bay to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Simpson Bay and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,740,132 searches. Data last updated May 28, 2024.
The lowest fares we've come across on flights traveling from Simpson Bay to Chicago in May and June 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Wed 7/103:05 pmSXM - ORD
1 stop19h 18mSpirit Airlines
Wed 7/175:00 amORD - SXM
1 stop8h 05mSpirit Airlines
Deal found 5/27$326
Wed 7/103:05 pmSXM - ORD
2 stops21h 55mSpirit Airlines
Wed 7/175:00 amORD - SXM
1 stop8h 05mSpirit Airlines
Deal found 5/27$331
Wed 7/103:05 pmSXM - ORD
2 stops25h 05mSpirit Airlines
Wed 7/1710:24 amORD - SXM
2 stops50h 41mSpirit Airlines
Deal found 5/27$475
Fri 11/85:00 pmSXM - ORD
2 stops16h 37mAmerican Airlines
Mon 11/116:55 amORD - SXM
1 stop7h 07mAmerican Airlines
Deal found 5/27$547
Fri 11/83:39 pmSXM - ORD
1 stop22h 33mAmerican Airlines
Mon 11/115:29 amORD - SXM
1 stop6h 31mAmerican Airlines
Deal found 5/27$553
Fri 11/85:00 pmSXM - ORD
2 stops16h 37mAmerican Airlines
Mon 11/115:29 amORD - SXM
2 stops8h 33mAmerican Airlines
Deal found 5/27$587
Fri 11/84:14 pmSXM - MDW
1 stop27h 02mKLM
Mon 11/111:05 pmMDW - SXM
1 stop23h 44mKLM
Deal found 5/27$590
Fri 11/81:20 pmSXM - MDW
2 stops31h 58mMultiple Airlines
Mon 11/118:13 pmMDW - SXM
2 stops37h 15mMultiple Airlines
Deal found 5/27$599
Fri 11/84:14 pmSXM - MDW
2 stops18h 31mDelta
Mon 11/116:50 pmMDW - SXM
1 stop17h 59mDelta
Deal found 5/27$816

One-way flights to Chicago from Simpson Bay

Search for one-way flight options from Simpson Bay to Chicago. 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 2,740,132 searches. Data last updated May 28, 2024.
Users traveling one-way from Simpson Bay to Chicago can select one of these great deals. For those needing a return trip from Simpson Bay, there is a search form available above.
Wed 9/42:44 pmSXM - ORD
1 stop10h 16mSpirit Airlines
Deal found 5/27$172
Wed 9/42:44 pmSXM - ORD
2 stops10h 39mSpirit Airlines
Deal found 5/27$199
Sat 6/154:20 pmSXM - ORD
1 stop27h 35mFrontier
Deal found 5/27$211
Sat 6/154:20 pmSXM - MDW
2 stops28h 36mFrontier
Deal found 5/27$213
Sat 6/154:20 pmSXM - ORD
1 stop27h 35mFrontier
Deal found 5/28$213
Wed 9/42:44 pmSXM - ORD
3 stops28h 28mSpirit Airlines
Deal found 5/27$237
Sat 7/204:30 pmSXM - ORD
1 stop26h 24mFrontier
Deal found 5/27$252
Sat 6/152:44 pmSXM - ORD
2 stops18h 40mSpirit Airlines
Deal found 5/28$258
Sat 6/152:44 pmSXM - ORD
2 stops18h 40mSpirit Airlines
Deal found 5/27$264

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 2,740,132 searches. Data last updated May 28, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$326 - $816

Route

Depart

Return

Price

Simpson Bay Princess JulianaChicago O'Hare Intl

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 7/10

1 stop19h 18m

Chicago O'Hare Intl

Wed 7/17

1 stop8h 05m

$326

Simpson Bay Princess JulianaChicago O'Hare Intl

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 7/10

2 stops21h 55m

Chicago O'Hare Intl

Wed 7/17

1 stop8h 05m

$331

Simpson Bay Princess JulianaChicago O'Hare Intl

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 7/10

2 stops25h 05m

Chicago O'Hare Intl

Wed 7/17

2 stops50h 41m

$475

Simpson Bay Princess JulianaChicago O'Hare Intl

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/8

2 stops16h 37m

Chicago O'Hare Intl

Mon 11/11

1 stop7h 07m

$547

Simpson Bay Princess JulianaChicago O'Hare Intl

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/8

1 stop22h 33m

Chicago O'Hare Intl

Mon 11/11

1 stop6h 31m

$553

Simpson Bay Princess JulianaChicago O'Hare Intl

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/8

2 stops16h 37m

Chicago O'Hare Intl

Mon 11/11

2 stops8h 33m

$587

Simpson Bay Princess JulianaChicago Midway

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 11/8

1 stop27h 02m

Chicago Midway

Mon 11/11

1 stop23h 44m

$590

Simpson Bay Princess JulianaChicago Midway

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 11/8

2 stops31h 58m

Chicago Midway

Mon 11/11

2 stops37h 15m

$599

Simpson Bay Princess JulianaChicago Midway

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 11/8

2 stops18h 31m

Chicago Midway

Mon 11/11

1 stop17h 59m

$816

Flights are sorted by cheapest first

Deals found on 5/27

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

Use this chart to determine the cheapest time to fly round-trip from Simpson Bay to Chicago. Price data was last updated on May 26, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Simpson Bay to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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.

Temperature and rainfall in Chicago by month

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

CHI

Temperature

23 - 73.4 °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 May 28, 2024.
Peruse reviews from past customers who have flown with Spirit 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
10,476 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,476 reviews
Delta
8.0
Very good
10,476 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Copa Airlines
8.0
Very good
2,638 reviews
Delta
8.0
Very good
10,476 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

KLM
7.9
Good
1,528 reviews
Delta
8.0
Very good
10,476 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

United Airlines
7.4
Good
10,799 reviews
Delta
8.0
Very good
10,476 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

American Airlines
7.3
Good
14,316 reviews
Delta
8.0
Very good
10,476 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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.

  • Can I find flights from Simpson Bay to Chicago for under $400 on Cheapflights?

    Yes, there are multiple flights from Simpson Bay to Chicago for under $400. The cheapest flight booked recently is on Spirit Airlines for just $326, but on average you can expect to pay $536.

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

    According to our current data, Spirit Airlines ($326), American Airlines ($547), and KLM ($590) offers the cheapest pricing from Simpson Bay to Chicago. Spirit Airlines is 53% 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 ($172), Frontier ($211), and United Airlines ($373).

  • What does SXM to ORD mean?

    Great question - SXM to ORD just means Simpson Bay Princess Juliana Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

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

    The amount of baggage you can bring on your Simpson Bay to Chicago 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 Simpson Bay to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Simpson Bay to Chicago 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 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.

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

    Many airlines flying from Simpson Bay to Chicago 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 Simpson Bay to Chicago?

    Yes, you can often find last-minute deals on Simpson Bay to Chicago 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 Simpson Bay to Chicago flight deals updated?

    The Simpson Bay to Chicago flight deals you see on this page were last updated on 5/27.

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

    Currently, February is the cheapest month in which you can book a flight from Simpson Bay to Chicago (average of $244). Flying from Simpson Bay to Chicago in June is currently the most expensive (average of $326). 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.

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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 2,740,132 searches. Data last updated May 28, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$372Average$773FlexibilityNo cancel feeOn-time71%
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Search flights from Simpson Bay to Chicago by cabin class

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

Explore weekly flight availability from Simpson Bay to Chicago. 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 28, 2024.
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Fly with Cheapflights

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How does Cheapflights help users find flights from Simpson Bay to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Simpson Bay today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Simpson Bay to Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Simpson Bay to Chicago.

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Simpson Bay to Chicago flexibly with Cheapflights today.

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

Yes, Cheapflights offers price alerts on Simpson Bay to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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