North Side Holidays from AU$3,688

Book a Hotel + Flight or Car together to unlock savings

Photo by Vincent Ramundo

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest North Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,440, price is now AU$3,688 per person
AU$3,688
per person
28 Dec - 3 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,580 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was AU$7,537, price is now AU$5,906 per person
AU$5,906
per person
28 Dec - 3 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,711, price is now AU$3,889 per person
AU$3,889
per person
28 Dec - 3 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
All good

Reviewed on 12 Nov 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$4,555, price is now AU$3,773 per person
AU$3,773
per person
28 Dec - 3 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)
Hello, the selection of breakfast from the cards they gave you for the price that you pay for pre paid with no option besides what’s on card

Reviewed on 12 Nov 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was AU$4,446, price is now AU$3,695 per person
AU$3,695
per person
28 Dec - 3 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Our guide on where to stay in North Side

Find the best North Side areas and neighborhoods for the activities you enjoy most. Learn more about North Side
A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

6 out of top 10 points of interest in this area

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Find hotels in Lincoln Park

North Side Holiday

North Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Lincoln Park Zoo, North Avenue Beach and Lincoln Park

Our pick of the best North Side Hotel Deals

The Willows Hotel

The Willows Hotel

3 out of 5
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$155 per night from 13 Dec to 14 Dec
AU$155
13 Dec - 14 Dec
includes taxes & fees
The Willows Hotel
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
3475 N. Clark St. Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 13 Dec to 14 Dec
AU$181
13 Dec - 14 Dec
includes taxes & fees
The Chicago Hotel Collection - Wrigleyville
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$211 per night from 22 Nov to 23 Nov
AU$211
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (1,159 reviews)
"The location is great, across Lincoln Park, close to restaurants, museums and stores. The hotel is nice, but needs some updates. The AC is very noisy, the bathrooms are old and in need of maintenance and updates. Cleaning service was bad and only changed towels, not even pick up the garbage. We had ..."

Reviewed on 12 Nov 2026

Hotel Lincoln
See all 569 properties in North 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
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular North Side attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
See properties

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in North Side

Frequently asked questions

How much does a North Side holiday package cost?
We make it simple to travel the world, with North Side holiday packages starting from just AU$3,688. You'll have the flexibility to bundle your favourite hotels, airlines and car rental. For the ultimate escape, why not add a few experiences and tours to your travel itinerary?
How do I get a cheap travel package to North Side?
Combining your hotel and flight with Expedia won't just save valuable time — it'll save you cash too. A North Side holiday package makes it a cinch to arrange your dream adventure. With more than 550 airlines around the world to choose from, finding flights that suit your schedule won't be an issue. On top of that, we've got over 1 000 000 hotels globally to pick from. Talk about choice! No matter who you are, Expedia brings the world within your reach.
Where should I stay in North Side?
Most people who visit North Side put both Wrigley Field and McCormick Place on their must-see lists. Why not choose a hotel near these iconic attractions?
What are the top hotels in North Side?
Get your trip off to a great start by reserving a room at Hotel Zachary Chicago, a Tribute Portfolio Hotel. It's one of most sought-after properties in North Side. Another leading option is The Chicago Hotel Collection - Wrigleyville.
How far in advance should I book my North Side holiday?
Search Expedia to compare airfares as soon as you know your travel dates. In most cases, you can purchase a seat up to 12 months before departure. If it's too early for your preferred air carrier, or you have to book last minute, don't stress. Low prices to North Side sometimes occur within weeks of the date of departure.
What does an Expedia North Side travel package include?
Rental cars, flights and hotels, or any combination of them — the choice is yours. Whether you're headed to North Side with the family or adventuring with your friends, there's a bundle to suit every style and budget. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a North Side travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and land great discounts. Hotels aren't your only option, though. We've got oceanfront condos, cosy city apartments and even houseboats and castles!
Can I choose my airline with a North Side Expedia holiday package?
Most definitely. Expedia has over 550 airline partners to select from across the world. With so much choice, finding the right carrier to get you to North Side will be a cinch.
If I'm not able to travel, can I cancel my North Side holiday package?
You can. We realise life happens, so we're here to help if you need to make changes to your North Side holiday package. It may be possible to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Look up our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.