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Cheap flights from Simpson Bay to Chicago from $334

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Simpson Bay to Chicago departing on 8/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Simpson Bay to Chicago

Cheap round-trip flights

Delta Logo
3:20 pm - 12:28 pmSXM-MDW
22h 08m2 stops
Delta Logo
6:00 am - 1:50 pmMDW-SXM
6h 50m1 stop
$599Delta
Find Deal
Mon, Sep 22 - Mon, Sep 29
Delta Logo
3:20 pm - 11:48 amSXM-MDW
21h 28m1 stop
Delta Logo
6:00 am - 1:50 pmMDW-SXM
6h 50m1 stop
$797Delta
Find Deal
Mon, Sep 22 - Mon, Sep 29
Delta Logo
3:21 pm - 3:23 pmSXM-MDW
25h 02m1 stop
Delta Logo
6:00 am - 1:56 pmMDW-SXM
6h 56m1 stop
$868Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
3:21 pm - 8:35 amSXM-MDW
18h 14m2 stops
Delta Logo
6:00 am - 1:50 pmMDW-SXM
6h 50m1 stop
$1,264Delta
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
3:21 pm - 9:36 amSXM-MDW
19h 15m1 stop
Delta Logo
11:00 am - 1:50 pmMDW-SXM
25h 50m1 stop
$1,367Delta
Find Deal
Sat, Sep 6 - Sat, Sep 13
Logo
6:10 pm - 5:37 pmSXM-MDW
24h 27m3 stops
Logo
1:43 pm - 1:14 pmMDW-SXM
22h 31m2 stops
$1,440
Find Deal
Sat, Sep 6 - Sat, Sep 13

Delta flights from Simpson Bay to Chicago Midway Airport

Our best Delta deals on Simpson Bay to Chicago Midway Airport flight tickets
Delta
Sep 22
SXM3:20 pmSimpson Bay Princess Juliana
22h 08m
2 stops
MDW12:28 pmChicago Midway
Sep 29
MDW6:00 amChicago Midway
6h 50m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
$599
Find similar
Delta
Sep 22
SXM3:20 pmSimpson Bay Princess Juliana
21h 28m
1 stop
MDW11:48 amChicago Midway
Sep 29
MDW6:00 amChicago Midway
6h 50m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
$797
Find similar
Delta
Aug 30
SXM3:21 pmSimpson Bay Princess Juliana
25h 02m
1 stop
MDW3:23 pmChicago Midway
Sep 6
MDW6:00 amChicago Midway
6h 56m
1 stop
SXM1:56 pmSimpson Bay Princess Juliana
$868
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 2, 2025.
Use the filters below to find and compare flights from Simpson Bay to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 9/22

3:20 pm-12:28 pm

2 stops22h 08m

Chicago Midway

Mon 9/29

6:00 am-1:50 pm

1 stop6h 50m

$599

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 9/22

3:20 pm-11:48 am

1 stop21h 28m

Chicago Midway

Mon 9/29

6:00 am-1:50 pm

1 stop6h 50m

$797

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 8/30

3:21 pm-3:23 pm

1 stop25h 02m

Chicago Midway

Sat 9/6

6:00 am-1:56 pm

1 stop6h 56m

$868

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/6

3:21 pm-8:35 am

2 stops18h 14m

Chicago Midway

Sat 9/13

6:00 am-1:50 pm

1 stop6h 50m

$1,264

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/6

3:21 pm-9:36 am

1 stop19h 15m

Chicago Midway

Sat 9/13

11:00 am-1:50 pm

1 stop25h 50m

$1,367

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/6

6:10 pm-5:37 pm

3 stops24h 27m

Chicago Midway

Sat 9/13

1:43 pm-1:14 pm

2 stops22h 31m

$1,440

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 8/16

3:05 pm-3:06 pm

2 stops25h 01m

$334

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 8/16

3:05 pm-3:06 pm

2 stops25h 01m

$342

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 8/17

2:10 pm-8:45 am

1 stop19h 35m

$511

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 8/17

8:35 pm-11:17 pm

2 stops27h 42m

$519

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Simpson Bay to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Simpson Bay Princess Juliana to Chicago Midway?

Delta is the most popular carrier operating from Simpson Bay Princess Juliana to Chicago Midway

When to book flights from Simpson Bay to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Simpson Bay to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Simpson Bay to Chicago Midway Airport (SXM to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Simpson Bay to Chicago Midway Airport

Best Price Found

$334

Fastest flight time

7h 44m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Simpson Bay in the past 72 hours is $334. The best round-trip flight deal from Simpson Bay to Chicago Midway Airport found on momondo in the last 72 hours is $599.
The fastest flight from Simpson Bay to Chicago Midway Airport takes 7h 44m
There are no direct flights from Simpson Bay to Chicago Midway Airport. Popular non-direct route for this connection is Simpson Bay Princess Juliana Airport - Chicago Midway Airport.
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  • How far is Simpson Bay Princess Juliana to Chicago Midway by plane?

    The distance between Simpson Bay Princess Juliana and Chicago Midway is about 2188.7 mi. Typically, this will take 18h 14m by plane in normal conditions.

  • When did momondo last update prices for flights from Simpson Bay Princess Juliana Airport to Chicago Midway Airport?

    Prices for flights from Simpson Bay Princess Juliana Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Simpson Bay Princess Juliana Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Simpson Bay Princess Juliana Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Why use momondo?

Why should I use momondo to find a flight deal from Simpson Bay to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Simpson Bay.

Can I find flights from Simpson Bay to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Simpson Bay with this policy.

How can momondo help me find flights from Simpson Bay to Chicago?

Once you have performed a search for Simpson Bay to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Simpson Bay to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Simpson Bay and alert you when they change.

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