Cheap Vacations in Sydney

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Sydney vacations

Price found within the past 48 hours. Click for updated prices.
Rydges Camperdown

Rydges Camperdown

4 out of 5
Camperdown
Price was $1,805, price is now $1,602 per person
$1,602
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was $2,617, price is now $1,929 per person
$1,929
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Establishment Hotel

Establishment Hotel

5 out of 5
Sydney Central Business District
Price was $2,393, price is now $1,958 per person
$1,958
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
APX Darling Harbour

APX Darling Harbour

3.5 out of 5
Sydney Central Business District
Price was $2,523, price is now $2,084 per person
$2,084
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Spicers Potts Point

Spicers Potts Point

4.5 out of 5
Potts Point
Price was $2,342, price is now $1,967 per person
$1,967
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Rydges Darling Square Apartment Hotel

Rydges Darling Square Apartment Hotel

4 out of 5
Sydney Central Business District
Price was $2,114, price is now $1,808 per person
$1,808
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Swissotel Sydney

Swissotel Sydney

5 out of 5
Sydney Central Business District
Price was $2,208, price is now $1,929 per person
$1,929
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Metro Apartments on King Street

Metro Apartments on King Street

3 out of 5
Sydney Central Business District
Price was $2,486, price is now $2,200 per person
$2,200
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Rydges Australia Square

Rydges Australia Square

4 out of 5
Sydney Central Business District
Price was $2,137, price is now $1,900 per person
$1,900
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Novotel Sydney City Centre

Novotel Sydney City Centre

4 out of 5
Sydney Central Business District
Price was $2,105, price is now $1,879 per person
$1,879
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)

3-night Sydney vacations

Price found within the past 48 hours. Click for updated prices.
Rydges Australia Square

Rydges Australia Square

4 out of 5
Price was $1,858, price is now $1,720 per person
$1,720
per person
Dec 5 - Dec 8
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
Price was $1,983, price is now $1,870 per person
$1,870
per person
Dec 5 - Dec 8
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Capella Sydney

Capella Sydney

5 out of 5
Price was $2,477, price is now $2,408 per person
$2,408
per person
Dec 5 - Dec 8
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)

4-night Sydney vacations

Price found within the past 48 hours. Click for updated prices.
Quest Mascot Serviced Apartments

Quest Mascot Serviced Apartments

4.5 out of 5
Price was $1,990, price is now $1,905 per person
$1,905
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Price was $2,478, price is now $2,201 per person
$2,201
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Price was $2,396, price is now $2,143 per person
$2,143
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Amora Hotel Jamison Sydney

Amora Hotel Jamison Sydney

5 out of 5
Price was $2,225, price is now $2,080 per person
$2,080
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Kith Hotel Darling Harbour

Kith Hotel Darling Harbour

3 out of 5
Price was $2,153, price is now $2,026 per person
$2,026
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Adina Sydney Darling Harbour

Adina Sydney Darling Harbour

3.5 out of 5
Price was $2,200, price is now $2,089 per person
$2,089
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Wildlife Retreat at Taronga

Wildlife Retreat at Taronga

4.5 out of 5
Price was $2,726, price is now $2,594 per person
$2,594
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
Price was $2,772, price is now $2,652 per person
$2,652
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Citadines Connect Sydney Airport

Citadines Connect Sydney Airport

4 out of 5
Price was $2,032, price is now $1,949 per person
$1,949
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
The Porter House Hotel Sydney - MGallery

The Porter House Hotel Sydney - MGallery

4.5 out of 5
Price was $2,327, price is now $2,235 per person
$2,235
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Novotel Sydney on Darling Harbour

Novotel Sydney on Darling Harbour

4.5 out of 5
Price was $2,387, price is now $2,293 per person
$2,293
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Quest North Sydney

Quest North Sydney

4 out of 5
Price was $2,084, price is now $2,004 per person
$2,004
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)

5-night Sydney vacations

Price found within the past 48 hours. Click for updated prices.
Rydges Camperdown

Rydges Camperdown

4 out of 5
Price was $1,805, price is now $1,602 per person
$1,602
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Price was $2,307, price is now $1,621 per person
$1,621
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Price was $2,617, price is now $1,929 per person
$1,929
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Price was $2,292, price is now $1,726 per person
$1,726
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Establishment Hotel

Establishment Hotel

5 out of 5
Price was $2,393, price is now $1,958 per person
$1,958
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Spicers Potts Point

Spicers Potts Point

4.5 out of 5
Price was $2,342, price is now $1,967 per person
$1,967
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Amora Hotel Jamison Sydney

Amora Hotel Jamison Sydney

5 out of 5
Price was $2,143, price is now $1,825 per person
$1,825
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Rydges Darling Square Apartment Hotel

Rydges Darling Square Apartment Hotel

4 out of 5
Price was $2,114, price is now $1,808 per person
$1,808
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Swissotel Sydney

Swissotel Sydney

5 out of 5
Price was $2,208, price is now $1,929 per person
$1,929
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Novotel Sydney on Darling Harbour

Novotel Sydney on Darling Harbour

4.5 out of 5
Price was $2,159, price is now $1,920 per person
$1,920
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Rydges Australia Square

Rydges Australia Square

4 out of 5
Price was $2,137, price is now $1,900 per person
$1,900
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Novotel Sydney City Centre

Novotel Sydney City Centre

4 out of 5
Price was $2,105, price is now $1,879 per person
$1,879
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)

6-7 night Sydney vacations

Price found within the past 48 hours. Click for updated prices.
Rydges Camperdown

Rydges Camperdown

4 out of 5
Price was $2,312, price is now $1,934 per person
$1,934
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Price was $4,083, price is now $2,907 per person
$2,907
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Price was $2,795, price is now $2,047 per person
$2,047
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Price was $2,875, price is now $2,108 per person
$2,108
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Establishment Hotel

Establishment Hotel

5 out of 5
Price was $3,085, price is now $2,468 per person
$2,468
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Rydges Australia Square

Rydges Australia Square

4 out of 5
Price was $2,748, price is now $2,224 per person
$2,224
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Rydges World Square

Rydges World Square

4.5 out of 5
Price was $2,988, price is now $2,436 per person
$2,436
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Spicers Potts Point

Spicers Potts Point

4.5 out of 5
Price was $3,040, price is now $2,499 per person
$2,499
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
APX Darling Harbour

APX Darling Harbour

3.5 out of 5
Price was $2,523, price is now $2,084 per person
$2,084
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Amora Hotel Jamison Sydney

Amora Hotel Jamison Sydney

5 out of 5
Price was $2,783, price is now $2,315 per person
$2,315
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Rydges Darling Square Apartment Hotel

Rydges Darling Square Apartment Hotel

4 out of 5
Price was $2,794, price is now $2,326 per person
$2,326
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)
Swissotel Sydney

Swissotel Sydney

5 out of 5
Price was $2,955, price is now $2,527 per person
$2,527
per person
Dec 3 - Dec 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sydney (SYD)

Flight deals to Sydney

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Nov 24 - Wed, Nov 25
AVV
Melbourne
SYD
Sydney
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Jetstar flight, departing Tue, Nov 24 from Melbourne to Sydney, returning Wed, Nov 25, priced at $126 found 1 day ago
Sat, Aug 21 - Sat, Aug 28
BNE
Brisbane
SYD
Sydney
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select Jetstar flight, departing Sat, Aug 21 from Brisbane to Sydney, returning Sat, Aug 28, priced at $130 found 1 day ago
Tue, Nov 24 - Wed, Nov 25
MEL
Melbourne
WSI
Sydney
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Jetstar flight, departing Tue, Nov 24 from Melbourne to Sydney, returning Wed, Nov 25, priced at $131 found 1 day ago

Top rated hotels for your Sydney vacation

Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
199 George St. Sydney NSW
Free Cancellation
Reserve now, pay when you stay
0.41 mi from city center
The price is $253 total per night
$253 total
per night
Oct 25 - Oct 26
With a stay at Four Seasons Hotel Sydney, you'll be centrally located in Sydney, steps from Circular Quay and Museum of Contemporary Art.
Pool
Hot Tub
Hyatt Regency Sydney

Hyatt Regency Sydney

5 out of 5
161 Sussex Street Sydney NSW
Free Cancellation
Reserve now, pay when you stay
0.3 mi from city center
The price is $192 total per night
$192 total
per night
Nov 1 - Nov 2
A stay at Hyatt Regency Sydney places you in the heart of Sydney, within a 10-minute walk of King Street Wharf and Pitt Street Mall.
Spa
Free WiFi
Shangri-La Sydney

Shangri-La Sydney

5 out of 5
176 Cumberland Street The Rocks NSW
Free Cancellation
Reserve now, pay when you stay
0.46 mi from city center
The price is $239 total per night
$239 total
per night
Oct 25 - Oct 26
With a stay at Shangri-La Sydney in Sydney (The Rocks), you'll be steps from The Big Dig Archaeology Education Centre and 4 minutes by foot from Circular Quay.
Pool
Spa
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Picks

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.