Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Simpson Bay to Chicago from $247

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 1/14. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Simpson Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:26 pm - 3:25 pmSXM-MDW
24h 59m2 stops
Delta Logo
5:59 pm - 11:15 amMDW-SXM
16h 16m2 stops
$632Delta
Find Deal
Fri, Mar 6 - Tue, Mar 10
Delta Logo
4:26 pm - 3:23 pmSXM-MDW
24h 57m2 stops
Delta Logo
6:00 am - 1:53 pmMDW-SXM
6h 53m1 stop
$722Delta
Find Deal
Fri, Mar 6 - Tue, Mar 10
Delta Logo
1:45 pm - 10:44 pmSXM-MDW
10h 59m1 stop
Delta Logo
6:00 am - 1:53 pmMDW-SXM
6h 53m1 stop
$812Delta
Find Deal
Fri, Mar 6 - Tue, Mar 10
Multiple Airlines Logo
1:05 pm - 10:05 amSXM-MDW
23h 00m2 stops
Multiple Airlines Logo
11:00 am - 11:55 amMDW-SXM
22h 55m2 stops
$839Multiple Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 24
Multiple Airlines Logo
4:20 pm - 1:10 pmSXM-MDW
22h 50m2 stops
Multiple Airlines Logo
11:48 am - 2:40 pmMDW-SXM
24h 52m3 stops
$978Multiple Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 24
Delta Logo
3:30 pm - 11:40 pmSXM-MDW
10h 10m1 stop
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
$983Delta
Find Deal
Sat, Nov 22 - Sat, Nov 29
Delta Logo
3:53 pm - 11:47 pmSXM-MDW
9h 54m1 stop
Delta Logo
6:00 am - 2:50 pmMDW-SXM
6h 50m1 stop
$1,008Delta
Find Deal
Wed, Dec 17 - Wed, Dec 24
Multiple Airlines Logo
3:40 pm - 6:18 pmSXM-MDW
28h 38m3 stops
Multiple Airlines Logo
1:47 pm - 3:21 pmMDW-SXM
23h 34m2 stops
$1,023Multiple Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
Multiple Airlines Logo
3:40 pm - 1:07 pmSXM-MDW
23h 27m3 stops
Multiple Airlines Logo
1:47 pm - 3:21 pmMDW-SXM
23h 34m2 stops
$1,028Multiple Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
WestJet Logo
4:20 pm - 6:18 pmSXM-MDW
27h 58m2 stops
WestJet Logo
10:47 am - 3:21 pmMDW-SXM
50h 34m2 stops
$3,830WestJet
Find Deal
Fri, Nov 21 - Sun, Nov 23

Delta flights from Simpson Bay to Chicago Midway Airport

Our best Delta deals on Simpson Bay to Chicago Midway Airport flight tickets
Delta
Mar 6
SXM4:26 pmSimpson Bay Princess Juliana
24h 59m
2 stops
MDW3:25 pmChicago Midway
Mar 10
MDW5:59 pmChicago Midway
16h 16m
2 stops
SXM11:15 amSimpson Bay Princess Juliana
$632
Find similar
Delta
Mar 6
SXM4:26 pmSimpson Bay Princess Juliana
24h 57m
2 stops
MDW3:23 pmChicago Midway
Mar 10
MDW9:20 amChicago Midway
24h 55m
2 stops
SXM11:15 amSimpson Bay Princess Juliana
$722
Find similar
Delta
Mar 6
SXM1:45 pmSimpson Bay Princess Juliana
10h 59m
1 stop
MDW10:44 pmChicago Midway
Mar 10
MDW6:00 amChicago Midway
6h 53m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
$812
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 November 3, 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

Fri 3/6

4:26 pm-3:25 pm

2 stops24h 59m

Chicago Midway

Tue 3/10

5:59 pm-11:15 am

2 stops16h 16m

$632

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:23 pm

2 stops24h 57m

Chicago Midway

Tue 3/10

6:00 am-1:53 pm

1 stop6h 53m

$722

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

1:45 pm-10:44 pm

1 stop10h 59m

Chicago Midway

Tue 3/10

6:00 am-1:53 pm

1 stop6h 53m

$812

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 12/17

1:05 pm-10:05 am

2 stops23h 00m

Chicago Midway

Wed 12/24

11:00 am-11:55 am

2 stops22h 55m

$839

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 12/17

4:20 pm-1:10 pm

2 stops22h 50m

Chicago Midway

Wed 12/24

11:48 am-2:40 pm

3 stops24h 52m

$978

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 11/22

3:30 pm-11:40 pm

1 stop10h 10m

Chicago Midway

Sat 11/29

6:00 am-2:55 pm

1 stop6h 55m

$983

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 12/17

3:53 pm-11:47 pm

1 stop9h 54m

Chicago Midway

Wed 12/24

6:00 am-2:50 pm

1 stop6h 50m

$1,008

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 11/22

3:40 pm-6:18 pm

3 stops28h 38m

Chicago Midway

Sat 11/29

1:47 pm-3:21 pm

2 stops23h 34m

$1,023

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 11/22

3:40 pm-1:07 pm

3 stops23h 27m

Chicago Midway

Sat 11/29

1:47 pm-3:21 pm

2 stops23h 34m

$1,028

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 11/21

4:20 pm-6:18 pm

2 stops27h 58m

Chicago Midway

Sun 11/23

10:47 am-3:21 pm

2 stops50h 34m

$3,830

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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?

Frontier, Delta, and Southwest 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

Direct flights

None
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 9h 20m 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
Crown Point
Munster
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 12/3
Wed 12/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago