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Cheap flights from Simpson Bay to Chicago from $204

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 2/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Simpson Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:35 pm - 11:40 pm
SXM
-
MDW
10h 05m
1 stop
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
$605Southwest
Fri, May 8 - Sun, May 10
Southwest Logo
2:35 pm - 7:55 am
SXM
-
MDW
18h 20m
2 stops
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
$610Southwest
Fri, May 8 - Sun, May 10
Delta Logo
12:55 pm - 10:31 pm
SXM
-
MDW
10h 36m
1 stop
Delta Logo
6:00 am - 1:54 pm
MDW
-
SXM
6h 54m
1 stop
$1,382Delta
Thu, Mar 19 - Thu, Mar 26
Delta Logo
1:38 pm - 10:31 pm
SXM
-
MDW
10h 53m
1 stop
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
$1,393Delta
Mon, Feb 16 - Thu, Feb 26
WestJet Logo
3:20 pm - 5:54 pm
SXM
-
MDW
27h 34m
2 stops
WestJet Logo
9:35 am - 2:17 pm
MDW
-
SXM
27h 42m
2 stops
$3,649WestJet
Thu, Mar 19 - Thu, Mar 26

Southwest flights from Simpson Bay to Chicago Midway Airport

Our best Southwest deals on Simpson Bay to Chicago Midway Airport flight tickets
Southwest
May 8
SXM2:35 pmSimpson Bay Princess Juliana
10h 05m
1 stop
MDW11:40 pmChicago Midway
May 10
MDW5:05 amChicago Midway
8h 20m
1 stop
SXM2:25 pmSimpson Bay Princess Juliana
$605
Southwest
May 8
SXM2:35 pmSimpson Bay Princess Juliana
18h 20m
2 stops
MDW7:55 amChicago Midway
May 10
MDW5:05 amChicago Midway
8h 20m
1 stop
SXM2:25 pmSimpson Bay Princess Juliana
$610

Delta flights from Simpson Bay to Chicago Midway Airport

Our best Delta deals on Simpson Bay to Chicago Midway Airport flight tickets
Delta
Mar 19
SXM12:55 pmSimpson Bay Princess Juliana
10h 36m
1 stop
MDW10:31 pmChicago Midway
Mar 26
MDW6:00 amChicago Midway
6h 54m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
$1,382
Delta
Feb 16
SXM1:38 pmSimpson Bay Princess Juliana
10h 53m
1 stop
MDW10:31 pmChicago Midway
Feb 26
MDW6:00 amChicago Midway
6h 50m
1 stop
SXM2:50 pmSimpson Bay Princess Juliana
$1,393

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 February 4, 2026.
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

Fri 5/8

2:35 pm-11:40 pm

1 stop10h 05m

Chicago Midway

Sun 5/10

5:05 am-2:25 pm

1 stop8h 20m

$605

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 5/8

2:35 pm-7:55 am

2 stops18h 20m

Chicago Midway

Sun 5/10

5:05 am-2:25 pm

1 stop8h 20m

$610

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 3/19

12:55 pm-10:31 pm

1 stop10h 36m

Chicago Midway

Thu 3/26

6:00 am-1:54 pm

1 stop6h 54m

$1,382

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 2/16

1:38 pm-10:31 pm

1 stop10h 53m

Chicago Midway

Thu 2/26

6:00 am-2:50 pm

1 stop6h 50m

$1,393

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 3/19

3:20 pm-5:54 pm

2 stops27h 34m

Chicago Midway

Thu 3/26

9:35 am-2:17 pm

2 stops27h 42m

$3,649

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 2/18

3:20 pm-11:27 am

2 stops22h 07m

$204

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 2/19

3:20 pm-10:25 pm

2 stops33h 05m

$226

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 2/19

1:38 pm-10:31 pm

1 stop10h 53m

$478

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 2/19

4:20 pm-10:25 pm

3 stops32h 05m

$497

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 3/26

12:55 pm-10:31 pm

1 stop10h 36m

$814

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 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

Fastest flight time

10h 05m

Direct flights

None
The fastest flight from Simpson Bay to Chicago Midway Airport takes 10h 05m
There are no direct flights from Simpson Bay to Chicago Midway Airport. There are no popular flight routes from Simpson Bay to Chicago Midway Airport.
Search flight deals

  • 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 10h 05m 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

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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