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

According to our current data, Spirit Airlines ($377), Frontier ($399), and American Airlines ($622) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 48% cheaper than the other options available to this destination.

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

$154 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and American Airlines, with prices starting from $163 and $307, respectively.

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

Travelers seeking maximum savings on their Chicago to Simpson Bay flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Chicago to Simpson Bay?

On average you can expect to pay $811 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $303 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $382.

What are the most popular airlines that fly from Chicago to Simpson Bay?

Consider American Airlines, Delta or Spirit Airlines when booking your flight. These represent the most popular airlines when flying from Chicago to Simpson Bay.

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

Departing on a Monday is a good option for securing a great price. You can expect to save up to 44% when planning your travel around this day of the week.

How far in advance should I book a flight from Chicago to Simpson Bay?

Travelers have found it’s best to book a flight 26 days in advance to save up to 74% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 26 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Simpson Bay 1-2 weeks in advance for as low as $389, or $1,114 for flights within the next 24 hours.

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

Flights from Chicago to Simpson Bay lean towards being more expensive in March. Prices are generally better when you fly from Chicago to Simpson Bay in September, with the cheapest ticket starting at $363.

Most accurate provider : When it comes to deals on Chicago-Simpson Bay flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-Simpson Bay flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Chicago-Simpson Bay flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago-Simpson Bay flights, Cheapflights users trust AranGrant the most. AranGrant 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 Chicago-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly into for flights to Simpson Bay from Chicago?

Most people fly into Simpson Bay Princess Juliana (SXM) if they book a flight to Simpson Bay from Chicago. On average, Princess Juliana has 0 inbound flights from Chicago per day from 4 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 Chicago to Simpson Bay that include hotel bookings?

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

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

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

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

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

$154+ Flights from Chicago to Simpson Bay - Compare & Save Big

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Find cheap flights from Chicago to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in September or October, booked 89 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Chicago to Simpson Bay

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$377 (Cheapflightsfares)
One-way from	$154 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$753
Good round-trip deal	$757 or less
Good one-way deal	$328 or less

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

Search Deals

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

Search Deals

From Chicago (CHI) to Simpson Bay Princess Juliana

Search Deals

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

Search Deals

Highest demand for flights based on searches. 3% potential increase in price ($27 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Price to beat on a round-trip flight from Chicago (CHI) to Simpson Bay Princess Juliana.

Search Deals

Price to beat on a one-way flight from Chicago (CHI) to Simpson Bay Princess Juliana.

Search Deals

Find flight deals from Chicago to Simpson Bay

Cheapest flights from Chicago to Simpson Bay
Explore the most affordable flight options available from Chicago to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

Fri 5/167:35 pmORD - SXM

1 stop17h 25mSpirit Airlines

Sat 5/243:05 pmSXM - ORD

1 stop10h 00mSpirit Airlines

Deal found 4/24

$377

Wed 7/165:05 amORD - SXM

1 stop7h 56mMultiple Airlines

Sat 7/2612:36 pmSXM - ORD

1 stop19h 32mMultiple Airlines

Deal found 4/24

$396

Fri 5/305:14 pmORD - SXM

1 stop17h 10mFrontier

Fri 6/66:15 pmSXM - ORD

2 stops31h 00mFrontier

Deal found 4/24

$399

Fri 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

Sat 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/25

$411

Sun 5/256:35 pmORD - SXM

1 stop17h 40mAmerican Airlines

Tue 6/34:40 pmSXM - ORD

1 stop17h 20mAmerican Airlines

Deal found 4/25

$622

Tue 7/296:00 amORD - SXM

1 stop6h 48mDelta

Sat 8/23:10 pmSXM - ORD

1 stop9h 45mDelta

Deal found 4/25

$722

Sat 12/66:20 pmORD - SXM

2 stops19h 35mAir Canada

Sat 12/135:15 pmSXM - ORD

2 stops19h 24mAir Canada

Deal found 4/25

$869

Thu 12/46:00 amMDW - SXM

1 stop6h 35mDelta

Sat 12/134:00 pmSXM - MDW

1 stop7h 44mDelta

Deal found 4/24

$1,037

Sat 4/2612:55 pmMDW - SXM

1 stop23h 20mMultiple Airlines

Mon 4/2812:05 pmSXM - MDW

2 stops23h 15mMultiple Airlines

Deal found 4/25

$1,617

Mon 12/295:04 pmMDW - SXM

2 stops20h 13mWestJet

Sun 1/44:10 pmSXM - MDW

2 stops20h 49mWestJet

Deal found 4/25

$4,325

Best flights from Chicago to Simpson Bay
Discover carefully curated flight deals from Chicago to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 25, 2025.

Fri 5/167:35 pmORD - SXM

1 stop17h 25mSpirit Airlines

Sat 5/243:05 pmSXM - ORD

1 stop10h 00mSpirit Airlines

Deal found 4/24

$377

Wed 7/165:05 amORD - SXM

1 stop7h 56mMultiple Airlines

Sat 7/2612:36 pmSXM - ORD

1 stop19h 32mMultiple Airlines

Deal found 4/24

$396

Fri 5/305:14 pmORD - SXM

1 stop17h 10mFrontier

Fri 6/66:15 pmSXM - ORD

2 stops31h 00mFrontier

Deal found 4/24

$399

Sun 5/256:35 pmORD - SXM

1 stop17h 40mAmerican Airlines

Tue 6/34:40 pmSXM - ORD

1 stop17h 20mAmerican Airlines

Deal found 4/25

$622

Fri 6/205:35 amORD - SXM

1 stop7h 25mDelta

Thu 6/263:25 pmSXM - ORD

1 stop9h 34mDelta

Deal found 4/23

$647

Fri 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

Sat 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/24

$411

Sun 5/46:04 amMDW - SXM

1 stop7h 01mDelta

Thu 5/83:19 pmSXM - MDW

2 stops18h 21mDelta

Deal found 4/25

$1,172

Last-minute flights from Chicago to Simpson Bay
Discover last-minute flight deals from Chicago to Simpson Bay. Data last updated April 25, 2025 and is based on user searches.

Sat 4/2610:37 amORD - SXM

Nonstop5h 12mUnited Airlines

Fri 5/21:35 pmSXM - ORD

1 stop11h 04mUnited Airlines

Deal found 4/25

$1,098

Sat 4/2612:55 pmMDW - SXM

1 stop23h 20mMultiple Airlines

Mon 4/2812:05 pmSXM - MDW

2 stops23h 15mMultiple Airlines

Deal found 4/25

$1,617

Sun 4/276:04 amMDW - SXM

1 stop7h 01mDelta

Sat 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/24

$1,092

Sat 5/35:36 amORD - SXM

1 stop7h 24mSpirit Airlines

Sat 5/103:05 pmSXM - ORD

1 stop10h 00mSpirit Airlines

Deal found 4/25

$461

Sun 5/45:30 amORD - SXM

1 stop7h 35mDelta

Thu 5/83:19 pmSXM - ORD

1 stop9h 39mDelta

Deal found 4/25

$967

Sun 5/46:04 amMDW - SXM

1 stop7h 01mDelta

Thu 5/83:19 pmSXM - MDW

2 stops18h 21mDelta

Deal found 4/25

$1,172

Mon 5/58:04 amORD - SXM

1 stop7h 57mMultiple Airlines

Thu 5/810:30 amSXM - ORD

2 stops24h 55mMultiple Airlines

Deal found 4/25

$789

Mon 5/56:51 amORD - SXM

1 stop7h 40mAmerican Airlines

Tue 5/133:24 pmSXM - ORD

1 stop9h 32mAmerican Airlines

Deal found 4/24

$842

Thu 5/155:30 amORD - SXM

1 stop7h 24mDelta

Tue 5/203:19 pmSXM - ORD

1 stop9h 39mDelta

Deal found 4/25

$732

Fri 5/167:35 pmORD - SXM

1 stop17h 25mSpirit Airlines

Sat 5/243:05 pmSXM - ORD

1 stop10h 00mSpirit Airlines

Deal found 4/24

$377

Sat 5/245:05 amORD - SXM

1 stop7h 55mMultiple Airlines

Sat 5/3112:34 pmSXM - ORD

1 stop12h 30mMultiple Airlines

Deal found 4/24

$433

Sun 5/256:35 pmORD - SXM

1 stop17h 40mAmerican Airlines

Tue 6/34:40 pmSXM - ORD

1 stop17h 20mAmerican Airlines

Deal found 4/25

$622

One-way flights from Chicago to Simpson Bay
Search for one-way flight options from Chicago to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated April 25, 2025.

Sat 6/215:05 amORD - SXM

1 stop7h 55mSpirit Airlines

Deal found 4/24

$154

Fri 5/235:14 pmORD - SXM

1 stop17h 10mFrontier

Deal found 4/24

$163

Mon 6/911:30 amORD - SXM

2 stops46h 53mMultiple Airlines

Deal found 4/25

$234

Sun 6/85:29 amORD - SXM

2 stops8h 36mAmerican Airlines

Deal found 4/24

$307

Sun 6/86:00 amMDW - SXM

1 stop7h 00mDelta

Deal found 4/24

$308

Mon 6/99:12 pmMDW - SXM

3 stops19h 38mMultiple Airlines

Deal found 4/25

$545

Mon 5/512:48 pmMDW - SXM

2 stops23h 27mWestJet

Deal found 4/25

$1,537

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/16

7:35 pm-2:00 pm

1 stop17h 25m

Simpson Bay Princess Juliana

Sat 5/24

3:05 pm-12:05 am

1 stop10h 00m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 7/16

5:05 am-2:01 pm

1 stop7h 56m

Simpson Bay Princess Juliana

Sat 7/26

12:36 pm-7:08 am

1 stop19h 32m

$396

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/30

5:14 pm-11:24 am

1 stop17h 10m

Simpson Bay Princess Juliana

Fri 6/6

6:15 pm-12:15 am

2 stops31h 00m

$399

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$411

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 5/25

6:35 pm-1:15 pm

1 stop17h 40m

Simpson Bay Princess Juliana

Tue 6/3

4:40 pm-9:00 am

1 stop17h 20m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 6/20

5:35 am-2:00 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 6/26

3:25 pm-11:59 pm

1 stop9h 34m

$647

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 5/4

6:04 am-2:05 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Thu 5/8

3:19 pm-8:40 am

2 stops18h 21m

$1,172

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/21

5:05 am-2:00 pm

1 stop7h 55m

$154

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/23

5:14 pm-11:24 am

1 stop17h 10m

$163

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 6/9

11:30 am-11:23 am

2 stops46h 53m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 14 results

Compare providers for flights from Chicago to Simpson Bay

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Simpson Bay in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
AranGrant	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 Chicago-Simpson Bay flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-Simpson Bay flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Chicago-Simpson Bay flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Chicago-Simpson Bay flights, Cheapflights users trust AranGrant the most. AranGrant 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 Chicago-Simpson Bay 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 Chicago to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Chicago 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 Chicago to Simpson Bay

How far ahead should I book a flight from Chicago to Simpson Bay?

The price you pay for your flight from Chicago to Simpson Bay may vary depending on when you book. For the best chance of a lower fare, look to book 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $459). Flying from Chicago to Simpson Bay in July is currently the most expensive (average of $675). 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.

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

When flying from Chicago to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 55% versus a flight in the morning.

Reviews of airlines servicing Simpson Bay

Get a feel of what it's like to fly with Delta, American Airlines and WestJet from Chicago to Simpson Bay by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,920 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet

7.2

Good

2,818 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Spirit Airlines

6.3

Okay

7,941 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Frontier

6.0

Okay

3,283 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

What airport do you fly into for flights to Simpson Bay from Chicago?
Most people fly into Simpson Bay Princess Juliana (SXM) if they book a flight to Simpson Bay from Chicago. On average, Princess Juliana has 0 inbound flights from Chicago per day from 4 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 Chicago to Simpson Bay round-trip?
According to our current data, Spirit Airlines ($377), Frontier ($399), and American Airlines ($622) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 48% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Chicago to Simpson Bay one-way?
$154 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and American Airlines, with prices starting from $163 and $307, respectively.
What are the cheapest flights from Chicago to Simpson Bay?
On average you can expect to pay $811 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $303 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $382.
Can I find deals for flights from Chicago to Simpson Bay that include hotel bookings?
Yes. In addition to deals on Chicago to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Simpson Bay?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Simpson Bay.
Can I find deals for business class flights from Chicago to Simpson Bay?
Yes. Cheapflights offers flight deals from Chicago to Simpson Bay 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 Chicago to Simpson Bay?
Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $459). Flying from Chicago to Simpson Bay in July is currently the most expensive (average of $675). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Chicago to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$325	Average$400	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$554	Average$775	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$604	Average$716	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$647	Average$897	FlexibilityNo cancel fee	On-time69%

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$154+ Cheap flights from Chicago (CHI) to Simpson Bay (SXM)

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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Simpson Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in September or October, booked 89 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Chicago to Simpson Bay

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Simpson Bay

Cheapest flights from Chicago to Simpson BayExplore the most affordable flight options available from Chicago to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

Explore the most affordable flight options available from Chicago to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

Cheapflights Fare Finder

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

Compare providers for flights from Chicago to Simpson Bay

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 Chicago to Simpson Bay in April.

Best time to book a flight from Chicago to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Chicago with our price prediction graph.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Simpson Bay. Price data was last updated on April 18, 2025.

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

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

Find hourly flight availability from Chicago to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2025.

Reviews of airlines servicing Simpson Bay

Related info for your journey

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

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

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

What are the cheapest flights from Chicago to Simpson Bay?

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Chicago to Simpson Bay

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Cheapest flights from Chicago to Simpson Bay
Explore the most affordable flight options available from Chicago to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.