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Cheap flights from St. John's to Chicago from $250

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 6/2. 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

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
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:30 am - 12:55 am
MDW
-
YYT
11h 55m
2 stops
$499Porter Airlines
Tue, May 12 - Tue, May 19
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:15 am - 12:56 am
MDW
-
YYT
12h 11m
2 stops
$564Porter Airlines
Tue, May 26 - Tue, Jun 2
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:15 am - 12:56 am
MDW
-
YYT
12h 11m
2 stops
$572Porter Airlines
Tue, May 26 - Tue, Jun 2
Multiple Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Multiple Airlines Logo
7:13 pm - 12:56 am
MDW
-
YYT
27h 13m
3 stops
$642Multiple Airlines
Tue, May 26 - Tue, Jun 2
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:15 am - 12:56 am
MDW
-
YYT
12h 11m
2 stops
$645Porter Airlines
Tue, May 26 - Tue, Jun 2
Multiple Airlines Logo
8:55 am - 9:45 am
YYT
-
MDW
27h 20m
3 stops
Multiple Airlines Logo
6:36 pm - 12:56 am
MDW
-
YYT
27h 50m
3 stops
$662Multiple Airlines
Tue, May 26 - Tue, Jun 2
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:30 am - 12:55 am
MDW
-
YYT
11h 55m
2 stops
$680Porter Airlines
Tue, May 12 - Tue, May 19
Porter Airlines Logo
4:05 pm - 9:45 am
YYT
-
MDW
20h 10m
3 stops
Porter Airlines Logo
3:20 pm - 12:55 am
MDW
-
YYT
7h 05m
2 stops
$687Porter Airlines
Tue, May 12 - Tue, May 19
Porter Airlines Logo
4:05 pm - 9:45 am
YYT
-
MDW
20h 10m
3 stops
Porter Airlines Logo
10:30 am - 3:10 pm
MDW
-
YYT
26h 10m
3 stops
$828Porter Airlines
Tue, May 12 - Tue, May 19
Delta Logo
3:00 pm - 1:11 pm
YYT
-
MDW
24h 41m
2 stops
Delta Logo
5:59 pm - 10:55 pm
MDW
-
YYT
26h 26m
2 stops
$840Delta
Tue, Sep 15 - Sat, Sep 19

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Delta flights from St. John's to Chicago Midway Airport

Our best Delta deals on St. John's to Chicago Midway Airport flight tickets
Delta
Sep 15
YYT3:00 pmSt John's
24h 41m
2 stops
MDW1:11 pmChicago Midway
Sep 19
MDW5:59 pmChicago Midway
26h 26m
2 stops
YYT10:55 pmSt John's
$840
Delta
Sep 15
YYT3:00 pmSt John's
24h 41m
2 stops
MDW1:11 pmChicago Midway
Sep 19
MDW5:59 pmChicago Midway
26h 26m
2 stops
YYT10:55 pmSt John's
$852
Delta
Sep 15
YYT3:00 pmSt John's
24h 41m
2 stops
MDW1:11 pmChicago Midway
Sep 19
MDW5:59 pmChicago Midway
26h 26m
2 stops
YYT10:55 pmSt John's
$918

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
May 12
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
May 19
MDW10:30 amChicago Midway
11h 55m
2 stops
YYT12:55 amSt John's
$499
Porter Airlines
May 26
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
Jun 2
MDW10:15 amChicago Midway
12h 11m
2 stops
YYT12:56 amSt John's
$564
Porter Airlines
May 26
YYT6:05 amSt John's
11h 00m
2 stops
MDW2:35 pmChicago Midway
Jun 2
MDW10:15 amChicago Midway
12h 11m
2 stops
YYT12:56 amSt John's
$572

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 May 1, 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
Quickest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/12

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Tue 5/19

10:30 am-12:55 am

2 stops11h 55m

$499

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/26

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Tue 6/2

10:15 am-12:56 am

2 stops12h 11m

$564

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/26

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Tue 6/2

10:15 am-12:56 am

2 stops12h 11m

$572

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/26

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Tue 6/2

7:13 pm-12:56 am

3 stops27h 13m

$642

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/26

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Tue 6/2

10:15 am-12:56 am

2 stops12h 11m

$645

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/26

8:55 am-9:45 am

3 stops27h 20m

Chicago Midway

Tue 6/2

6:36 pm-12:56 am

3 stops27h 50m

$662

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/12

6:05 am-2:35 pm

2 stops11h 00m

Chicago Midway

Tue 5/19

10:30 am-12:55 am

2 stops11h 55m

$680

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/12

4:05 pm-9:45 am

3 stops20h 10m

Chicago Midway

Tue 5/19

3:20 pm-12:55 am

2 stops7h 05m

$687

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 5/12

4:05 pm-9:45 am

3 stops20h 10m

Chicago Midway

Tue 5/19

10:30 am-3:10 pm

3 stops26h 10m

$828

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 9/15

3:00 pm-1:11 pm

2 stops24h 41m

Chicago Midway

Sat 9/19

5:59 pm-10:55 pm

2 stops26h 26m

$840

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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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?

Porter Airlines 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
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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.

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