SYD - MDW

$609 Find Cheap Flights from Sydney to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$2,609
Typical prices: $1,469-$1,546
Singapore Airlines
Mon 11/19Sun 12/2
SYD - MDW • 2 stops
Cheapest one-way
$903
Typical prices: $795-$1,214
Multiple Airlines
Sun 3/4
SYD - MDW • 2 stops
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Flight Deals

Cheap Flights from Sydney to Midway (SYD-MDW)

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

Recent round-trip flight deals from Sydney to Midway

Thu, Nov 19 - Wed, Dec 2
Singapore Airlines Logo
12:15 pm - 5:55 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
34h 40m2 stops Singapore Changi Los Angeles
Singapore Airlines Logo
3:45 pm - 5:55 pmMDW  Chicago Midway-SYD Sydney Kingsford Smith
33h 10m2 stops Los Angeles Singapore Changi
$2,609Singapore Airlines
Wed, Dec 23 - Wed, Dec 30
Multiple Airlines Logo
2:05 pm - 12:01 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
26h 56m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:01 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
31h 54m1 stop Dallas/Fort Worth
$2,727Multiple Airlines
Thu, Nov 19 - Wed, Dec 2
Multiple Airlines Logo
2:05 pm - 7:23 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
34h 18m1 stop Dallas/Fort Worth
Multiple Airlines Logo
10:21 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
27h 34m1 stop Dallas/Fort Worth
$2,747Multiple Airlines
Wed, Dec 23 - Wed, Dec 30
Multiple Airlines Logo
2:05 pm - 12:01 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
26h 56m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:01 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
31h 54m1 stop Dallas/Fort Worth
$2,754Multiple Airlines
Thu, Nov 19 - Wed, Dec 2
Multiple Airlines Logo
2:05 pm - 11:47 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
26h 42m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson
Multiple Airlines Logo
10:21 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
27h 34m1 stop Dallas/Fort Worth
$2,774Multiple Airlines
Thu, Apr 1 - Mon, May 10
Singapore Airlines Logo
12:00 pm - 6:00 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
34h 00m2 stops Singapore Changi San Francisco
Singapore Airlines Logo
3:55 pm - 7:15 pmMDW  Chicago Midway-SYD Sydney Kingsford Smith
36h 20m2 stops Los Angeles Singapore Changi
$2,872Singapore Airlines
Sat, Dec 5 - Sat, Dec 12
Multiple Airlines Logo
2:05 pm - 7:42 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
46h 37m2 stops Dallas/Fort Worth Orlando
Multiple Airlines Logo
10:40 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
27h 15m1 stop Dallas/Fort Worth
$3,130Multiple Airlines
Thu, Nov 26 - Thu, Dec 3
Singapore Airlines Logo
12:15 pm - 6:00 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
34h 45m2 stops Singapore Changi Los Angeles
Singapore Airlines Logo
3:45 pm - 9:15 pmMDW  Chicago Midway-SYD Sydney Kingsford Smith
36h 30m2 stops Los Angeles Singapore Changi
$3,132Singapore Airlines
Fri, Dec 18 - Fri, Jan 1
Multiple Airlines Logo
2:05 pm - 12:03 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
38h 58m1 stop Dallas/Fort Worth
Multiple Airlines Logo
1:11 pm - 5:45 pmMDW  Chicago Midway-SYD Sydney Kingsford Smith
35h 34m2 stops Atlanta Hartsfield-Jackson Abu Dhabi Zayed Intl
$3,585Multiple Airlines
Fri, Dec 18 - Fri, Jan 1
Multiple Airlines Logo
9:45 am - 12:01 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
31h 16m3 stops Auckland Intl Los Angeles Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:01 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
31h 54m1 stop Dallas/Fort Worth
$3,620Multiple Airlines
Booking Insights

Price, demand and travel trends for Sydney to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Sydney to Chicago Midway Airport?

Round-trip flights from Sydney to Chicago Midway Airport typically range from $1,469 to $1,546. The lowest price found in the past 5 days was $2,609, on Singapore Airlines.

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Key details for Sydney to Chicago Midway Airport flights

Cheapest flight

$903
One-way flight from Sydney to Chicago Midway Airport

When to book flights from Sydney to Midway

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

Your Sydney 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 Sydney 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.

  • Have flight prices from Sydney to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $2,609 to $8,928. That means the highest observed fare was about 3x higher than the lowest one.

  • How are flight prices from Sydney to Chicago Midway Airport looking right now?

    One-way fares from Sydney to Chicago Midway Airport are currently higher than usual. Average one-way flight prices are about $1,004, which is 15% above the typical average for this route.

  • 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 Sydney to Chicago Midway Airport?

    Flights from Sydney to Chicago Midway Airport usually depart from Sydney Kingsford Smith (SYD) and arrive at Chicago Midway (MDW).

  • What is the time difference between Sydney and Chicago Midway Airport?

    Chicago Midway Airport is 17 hours behind Sydney (Central Time vs Eastern Australia 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 Sydney 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 Sydney to Midway

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

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