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.

$243 Cheap Flights from Simpson Bay to Chicago Midway Airport in 2026

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0 bags

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Find the cheapest flights from Simpson Bay to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:25 pm - 12:05 am

SXM

MDW

10h 40m

1 stop

5:35 am - 1:30 pm

MDW

SXM

6h 55m

1 stop

$618Southwest

Fri, May 8 - Mon, May 11

2:25 pm - 12:05 am

SXM

MDW

10h 40m

1 stop

5:15 pm - 1:30 pm

MDW

SXM

19h 15m

2 stops

$623Southwest

Fri, May 8 - Mon, May 11

2:25 pm - 7:35 am

SXM

MDW

18h 10m

2 stops

6:00 am - 1:30 pm

MDW

SXM

6h 30m

1 stop

$630Southwest

Tue, May 5 - Tue, May 12

2:25 pm - 12:05 am

SXM

MDW

10h 40m

1 stop

9:25 pm - 12:25 pm

MDW

SXM

14h 00m

1 stop

$645Southwest

Fri, May 15 - Fri, May 29

2:25 pm - 7:55 am

SXM

MDW

18h 30m

2 stops

4:35 pm - 12:25 pm

MDW

SXM

18h 50m

2 stops

$650Southwest

Fri, May 15 - Fri, May 29

3:20 pm - 6:33 pm

SXM

MDW

28h 13m

2 stops

6:36 pm - 1:51 pm

MDW

SXM

18h 15m

2 stops

$670Delta

Tue, May 12 - Sun, May 31

2:25 pm - 7:35 am

SXM

MDW

18h 10m

2 stops

8:55 pm - 1:30 pm

MDW

SXM

15h 35m

2 stops

$675Southwest

Tue, May 5 - Tue, May 12

3:00 pm - 12:40 am

SXM

MDW

10h 40m

1 stop

5:10 am - 2:00 pm

MDW

SXM

7h 50m

1 stop

$690Southwest

Thu, Jun 4 - Tue, Jun 30

3:20 pm - 8:43 am

SXM

MDW

18h 23m

2 stops

6:36 pm - 1:51 pm

MDW

SXM

18h 15m

2 stops

$695Delta

Tue, May 12 - Sat, May 30

1:35 pm - 10:28 pm

SXM

MDW

9h 53m

1 stop

6:38 pm - 12:10 pm

MDW

SXM

16h 32m

2 stops

$706Delta

Sat, Apr 18 - Sat, Apr 25

momondo Fare Finder

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

Cheapest round-trip

Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 5/8

2:25 pm-12:05 am

1 stop10h 40m

Chicago Midway

Mon 5/11

5:35 am-1:30 pm

1 stop6h 55m

$618

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 5/8

2:25 pm-12:05 am

1 stop10h 40m

Chicago Midway

Mon 5/11

5:15 pm-1:30 pm

2 stops19h 15m

$623

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 5/5

2:25 pm-7:35 am

2 stops18h 10m

Chicago Midway

Tue 5/12

6:00 am-1:30 pm

1 stop6h 30m

$630

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 5/15

2:25 pm-12:05 am

1 stop10h 40m

Chicago Midway

Fri 5/29

9:25 pm-12:25 pm

1 stop14h 00m

$645

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 5/15

2:25 pm-7:55 am

2 stops18h 30m

Chicago Midway

Fri 5/29

4:35 pm-12:25 pm

2 stops18h 50m

$650

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-6:33 pm

2 stops28h 13m

Chicago Midway

Sun 5/31

6:36 pm-1:51 pm

2 stops18h 15m

$670

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 5/5

2:25 pm-7:35 am

2 stops18h 10m

Chicago Midway

Tue 5/12

8:55 pm-1:30 pm

2 stops15h 35m

$675

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 6/4

3:00 pm-12:40 am

1 stop10h 40m

Chicago Midway

Tue 6/30

5:10 am-2:00 pm

1 stop7h 50m

$690

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-8:43 am

2 stops18h 23m

Chicago Midway

Sat 5/30

6:36 pm-1:51 pm

2 stops18h 15m

$695

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 4/18

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Sat 4/25

6:38 pm-12:10 pm

2 stops16h 32m

$706

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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?

Southwest 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 40m
Direct flights	None

The fastest flight from Simpson Bay to Chicago Midway Airport takes 10h 40m

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 40m 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.

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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.