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.

$342 Cheap Flights from Simpson Bay to Chicago Midway Airport in 2026

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.

3:05 pm - 10:45 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 40m1 stop Orlando

5:10 am - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

7h 55m1 stop Orlando

$467Southwest

Mon, Sep 28 - Sun, Oct 4

3:05 pm - 10:45 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 40m1 stop Orlando

9:20 pm - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

15h 45m2 stops Baltimore/Washington Orlando

$472Southwest

Mon, Sep 28 - Sun, Oct 4

3:05 pm - 11:30 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

21h 25m2 stops Orlando Las Vegas Harry Reid Intl

6:25 pm - 1:45 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

18h 20m2 stops Denver Intl Orlando

$489Southwest

Fri, Oct 9 - Fri, Oct 16

3:05 pm - 12:20 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

10h 15m1 stop Orlando

5:00 am - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

8h 05m1 stop Orlando

$501Southwest

Fri, Oct 9 - Fri, Oct 16

3:05 pm - 12:20 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

10h 15m1 stop Orlando

5:50 pm - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

19h 15m2 stops Las Vegas Harry Reid Intl Orlando

$531Southwest

Thu, Oct 15 - Wed, Oct 21

3:05 pm - 12:20 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

10h 15m1 stop Orlando

5:00 am - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

8h 05m1 stop Orlando

$543Southwest

Fri, Oct 9 - Fri, Oct 16

3:05 pm - 7:15 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

17h 10m2 stops Orlando Baltimore/Washington

5:50 pm - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

19h 15m2 stops Las Vegas Harry Reid Intl Orlando

$555Southwest

Thu, Oct 15 - Wed, Oct 21

3:05 pm - 12:20 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

10h 15m1 stop Orlando

5:00 am - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

8h 05m1 stop Orlando

$560Southwest

Fri, Oct 9 - Fri, Oct 16

3:05 pm - 12:20 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

10h 15m1 stop Orlando

5:50 pm - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

19h 15m2 stops Las Vegas Harry Reid Intl Orlando

$571Southwest

Thu, Oct 15 - Wed, Oct 21

3:05 pm - 7:15 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

17h 10m2 stops Orlando Baltimore/Washington

5:50 pm - 2:05 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

19h 15m2 stops Las Vegas Harry Reid Intl Orlando

$588Southwest

Thu, Oct 15 - Wed, Oct 21

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Southwest flights from Simpson Bay to Chicago Midway Airport

Our best Southwest deals on Simpson Bay to Chicago Midway Airport flight tickets

Southwest

Sep 28

SXM3:05 pmSimpson Bay Princess Juliana

8h 40m

1 stop

MDW10:45 pmChicago Midway

Oct 4

MDW5:10 amChicago Midway

7h 55m

1 stop

SXM2:05 pmSimpson Bay Princess Juliana

$467

Southwest

Sep 28

SXM3:05 pmSimpson Bay Princess Juliana

8h 40m

1 stop

MDW10:45 pmChicago Midway

Oct 4

MDW9:20 pmChicago Midway

15h 45m

2 stops

SXM2:05 pmSimpson Bay Princess Juliana

$472

Southwest

Oct 9

SXM3:05 pmSimpson Bay Princess Juliana

21h 25m

2 stops

MDW11:30 amChicago Midway

Oct 16

MDW6:25 pmChicago Midway

18h 20m

2 stops

SXM1:45 pmSimpson Bay Princess Juliana

$489

Delta flights from Simpson Bay to Chicago Midway Airport

Our best Delta deals on Simpson Bay to Chicago Midway Airport flight tickets

Delta

Oct 15

SXM3:05 pmSimpson Bay Princess Juliana

8h 28m

1 stop

MDW10:33 pmChicago Midway

Oct 21

MDW6:04 amChicago Midway

6h 36m

1 stop

SXM1:40 pmSimpson Bay Princess Juliana

$656

Delta

Sep 28

SXM3:18 pmSimpson Bay Princess Juliana

18h 49m

2 stops

MDW9:07 amChicago Midway

Oct 4

MDW7:01 pmChicago Midway

17h 52m

2 stops

SXM1:53 pmSimpson Bay Princess Juliana

$742

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 Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Mon 9/28

3:05 pm-10:45 pm

1 stop8h 40m

Chicago Midway

Sun 10/4

5:10 am-2:05 pm

1 stop7h 55m

$467

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Mon 9/28

3:05 pm-10:45 pm

1 stop8h 40m

Chicago Midway

Sun 10/4

9:20 pm-2:05 pm

2 stops15h 45m

$472

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 10/9

3:05 pm-11:30 am

2 stops21h 25m

Chicago Midway

Fri 10/16

6:25 pm-1:45 pm

2 stops18h 20m

$489

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 10/9

3:05 pm-12:20 am

1 stop10h 15m

Chicago Midway

Fri 10/16

5:00 am-2:05 pm

1 stop8h 05m

$501

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 10/15

3:05 pm-12:20 am

1 stop10h 15m

Chicago Midway

Wed 10/21

5:50 pm-2:05 pm

2 stops19h 15m

$531

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 10/9

3:05 pm-12:20 am

1 stop10h 15m

Chicago Midway

Fri 10/16

5:00 am-2:05 pm

1 stop8h 05m

$543

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 10/15

3:05 pm-7:15 am

2 stops17h 10m

Chicago Midway

Wed 10/21

5:50 pm-2:05 pm

2 stops19h 15m

$555

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 10/9

3:05 pm-12:20 am

1 stop10h 15m

Chicago Midway

Fri 10/16

5:00 am-2:05 pm

1 stop8h 05m

$560

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 10/15

3:05 pm-12:20 am

1 stop10h 15m

Chicago Midway

Wed 10/21

5:50 pm-2:05 pm

2 stops19h 15m

$571

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 10/15

3:05 pm-7:15 am

2 stops17h 10m

Chicago Midway

Wed 10/21

5:50 pm-2:05 pm

2 stops19h 15m

$588

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 and Delta are the most popular carriers 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	$342
Fastest flight time	8h 26m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Simpson Bay in the past 72 hours is $342. The best round-trip flight deal from Simpson Bay to Chicago Midway Airport found on momondo in the last 72 hours is $467.

The fastest flight from Simpson Bay to Chicago Midway Airport takes 8h 26m

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

Frequently asked questions about flying from Simpson Bay to Chicago Midway Airport

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 8h 26m 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.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

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.