Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from St. John's to Chicago from $405

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from St. John's to Chicago departing on 9/14. 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
1 adult, Economy, 0 bags

Find the cheapest flights from St. John's to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
7:00 pm - 2:35 pm
YYT
-
MDW
22h 05m
1 stop
Porter Airlines Logo
3:20 pm - 10:55 pm
MDW
-
YYT
29h 05m
2 stops
$498Porter Airlines
Thu, Jul 16 - Wed, Jul 22
Porter Airlines Logo
7:00 pm - 2:35 pm
YYT
-
MDW
22h 05m
1 stop
Porter Airlines Logo
10:25 am - 12:08 am
MDW
-
YYT
11h 13m
1 stop
$514Porter Airlines
Thu, Jul 16 - Wed, Jul 22
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:25 am - 12:55 am
MDW
-
YYT
12h 00m
2 stops
$525Porter Airlines
Thu, Jul 16 - Wed, Jul 22
Porter Airlines Logo
10:00 am - 9:40 am
YYT
-
MDW
26h 10m
1 stop
Porter Airlines Logo
10:25 am - 10:55 pm
MDW
-
YYT
34h 00m
2 stops
$556Porter Airlines
Thu, Jul 2 - Sat, Jul 11
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:25 am - 12:55 am
MDW
-
YYT
12h 00m
2 stops
$558Porter Airlines
Thu, Jul 2 - Sat, Jul 11
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:15 pm - 12:55 am
MDW
-
YYT
7h 10m
2 stops
$560Porter Airlines
Thu, Jul 30 - Thu, Aug 6
Porter Airlines Logo
10:00 am - 9:40 am
YYT
-
MDW
26h 10m
1 stop
Porter Airlines Logo
10:25 am - 10:18 pm
MDW
-
YYT
9h 23m
1 stop
$693Porter Airlines
Thu, Jul 2 - Sat, Jul 11
Multiple Airlines Logo
4:00 pm - 9:40 am
YYT
-
MDW
20h 10m
3 stops
Multiple Airlines Logo
10:20 am - 12:55 am
MDW
-
YYT
12h 05m
2 stops
$756Multiple Airlines
Thu, Jul 30 - Thu, Aug 6
Multiple Airlines Logo
5:00 pm - 6:25 pm
YYT
-
MDW
27h 55m
3 stops
Multiple Airlines Logo
3:15 pm - 3:05 pm
MDW
-
YYT
21h 20m
3 stops
$971Multiple Airlines
Thu, Jul 30 - Thu, Aug 6

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

Porter Airlines flights from St. John's to Chicago Midway Airport

Our best Porter Airlines deals on St. John's to Chicago Midway Airport flight tickets
Porter Airlines
Jul 16
YYT7:00 pmSt John's
22h 05m
1 stop
MDW2:35 pmChicago Midway
Jul 22
MDW3:20 pmChicago Midway
29h 05m
2 stops
YYT10:55 pmSt John's
$498
Porter Airlines
Jul 16
YYT7:00 pmSt John's
22h 05m
1 stop
MDW2:35 pmChicago Midway
Jul 22
MDW10:25 amChicago Midway
11h 13m
1 stop
YYT12:08 amSt John's
$514
Porter Airlines
Jul 16
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
Jul 22
MDW10:25 amChicago Midway
12h 00m
2 stops
YYT12:55 amSt John's
$525

momondo Fare Finder

 
Customize your flight search to find flights from St. John's 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 June 16, 2026.
Use the filters below to find and compare flights from St. John's to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/16

7:00 pm-2:35 pm

1 stop22h 05m

Chicago Midway

Wed 7/22

3:20 pm-10:55 pm

2 stops29h 05m

$498

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/16

7:00 pm-2:35 pm

1 stop22h 05m

Chicago Midway

Wed 7/22

10:25 am-12:08 am

1 stop11h 13m

$514

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/16

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Wed 7/22

10:25 am-12:55 am

2 stops12h 00m

$525

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/2

10:00 am-9:40 am

1 stop26h 10m

Chicago Midway

Sat 7/11

10:25 am-10:55 pm

2 stops34h 00m

$556

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/2

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Sat 7/11

10:25 am-12:55 am

2 stops12h 00m

$558
Quickest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/30

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Thu 8/6

3:15 pm-12:55 am

2 stops7h 10m

$560

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/2

10:00 am-9:40 am

1 stop26h 10m

Chicago Midway

Sat 7/11

10:25 am-10:18 pm

1 stop9h 23m

$693

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/30

4:00 pm-9:40 am

3 stops20h 10m

Chicago Midway

Thu 8/6

10:20 am-12:55 am

2 stops12h 05m

$756

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 7/30

5:00 pm-6:25 pm

3 stops27h 55m

Chicago Midway

Thu 8/6

3:15 pm-3:05 pm

3 stops21h 20m

$971
Cheapest one-way

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Mon 9/14

3:00 pm-9:53 am

2 stops21h 23m

$405

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from St. John's 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 St John's to Chicago Midway?

WestJet is the most popular carrier operating from St John's to Chicago Midway

When to book flights from St. John's to Chicago Midway Airport

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

Cheap St. John's to Chicago Midway Airport (YYT to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from St. John's to Chicago Midway Airport

Fastest flight time

11h 00m

Direct flights

None
The fastest flight from St. John's to Chicago Midway Airport takes 11h 00m
There are no direct flights from St. John's to Chicago Midway Airport. There are no popular flight routes from St. John's to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from St. John's to Chicago Midway Airport

  • How far is St John's to Chicago Midway by plane?

    The straight-line distance from St John's to Chicago Midway is 1749.9 mi. A reasonable flight in good conditions will take 11h 00m.

  • When did momondo last update prices for flights from St John's Airport to Chicago Midway Airport?

    Prices for flights from St John's Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from St John's 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 St John's Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable 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
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from St. John's to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from St. John's to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from St. John's to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from St. John's with this policy.

How can momondo help me find flights from St. John's to Chicago?

Once all potential St. John's to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from St. John's to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of St. John's to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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
Thu 7/16
Thu 7/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago