YYT - MDW

$525 Find Cheap Flights from St. John's to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$802
Typical prices: $710-$710
Multiple Airlines
Mon 12/3Mon 12/10
YYT - MDW • 3 stops
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Flight Deals

Cheap Flights from St. John's to Chicago (YYT-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from St. John's to Chicago

Thu, Dec 3 - Thu, Dec 10
Multiple Airlines Logo
3:15 pm - 2:41 pmYYT  St John's-MDW Chicago Midway
25h 56m3 stops Halifax Intl Toronto Pearson Intl Orlando
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8:37 pm - 12:58 amMDW  Chicago Midway-YYT St John's
25h 51m3 stops Orlando Toronto Pearson Intl Ottawa
$802Multiple Airlines
Sat, Dec 12 - Mon, Dec 14
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6:00 am - 9:37 amYYT  St John's-MDW Chicago Midway
30h 07m3 stops Ottawa Toronto Pearson Intl Detroit Metropolitan Wayne County
Multiple Airlines Logo
6:41 pm - 1:35 pmMDW  Chicago Midway-YYT St John's
16h 24m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
$1,054Multiple Airlines
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Key details for St. John's to Chicago Midway Airport flights

Cheapest flight

$525
One-way flight from St. John's to Chicago Midway Airport

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

Are your dates flexible? Find out the best times to travel from St. John's to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your St. John's to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Do I need a passport to fly from St. John's to Chicago Midway Airport?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $86 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from St. John's to Chicago Midway Airport?

    Flights from St. John's to Chicago Midway Airport usually depart from St John's (YYT) and arrive at Chicago Midway (MDW).

  • What is the time difference between St. John's and Chicago Midway Airport?

    Chicago Midway Airport is 2 hours behind St. John's (Central Time vs Newfoundland Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking St. John's to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.

More options for your flight from St. John's to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
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