Northwest Side Holidays from AU$1,834

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The Latest Northwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was AU$3,921, price is now AU$1,834 per person
AU$1,834
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,617 reviews)
Comfortable room & bathroom. Everything was fine

Reviewed on 19 Aug. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$4,298, price is now AU$1,981 per person
AU$1,981
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location

Reviewed on 20 Aug. 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,238, price is now AU$1,969 per person
AU$1,969
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.

Reviewed on 20 Aug. 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was AU$4,602, price is now AU$2,176 per person
AU$2,176
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on 17 Aug. 2025

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Price was AU$3,936, price is now AU$1,864 per person
AU$1,864
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8/10 Very Good! (8,976 reviews)
Family had a great stay.

Reviewed on 21 Aug. 2025

Our guide on where to stay in Northwest Side

Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
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Irving Park

2 out of top 10 points of interest in this area

Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.

Find hotels in Irving Park

Northwest Side Holiday

Northwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Our pick of the best Northwest Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$217 per night from 24 Aug to 25 Aug
AU$217
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug. 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 1 Sept to 2 Sept
AU$276
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"Love it"

Reviewed on 19 Aug. 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is AU$293 per night from 3 Sept to 4 Sept
AU$293
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,733 reviews)
"Great"

Reviewed on 20 Aug. 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,011 properties in Northwest Side
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Northwest Side

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Northwest Side

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Northwest Side

Frequently asked questions

How much does a Northwest Side holiday package cost?
Explore the best of Northwest Side from just AU$1,834. Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few experiences or tours to your package.
How do I get a cheap travel package to Northwest Side?
Book everything all in one place with our Northwest Side holiday packages. We have deals on flights, hotels, tours and more that'll keep your pocketbook happy and your sense of adventure alive. And, with more than 550 air carriers and 1 000 000 hotel options globally to choose from, you'll have the flexibility to mix and match as you like.
How far in advance should I book my Northwest Side holiday?
Savvy travellers often reserve their seats early. You can generally look up international airfares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Northwest Side travel package include?
Hotels, rental cars and flights, or any combination of the three — you decide! Whether you're headed to Northwest Side on a family road trip or travelling solo, there's a package to fit every budget and style. Once you've made your booking, why not add on some activities?
Can I choose my airline with a Northwest Side Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the flexibility to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Northwest Side holiday package?
Because we understand life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.