North Side Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Vincent Ramundo

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

North Side Holiday

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 NZ$194 per night from 1 Dec to 2 Dec
NZ$194
1 Dec - 2 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 NZ$229 per night from 6 Dec to 7 Dec
NZ$229
6 Dec - 7 Dec
includes taxes & fees
7.4/10 Good! (1,004 reviews)
"Great overall"

Reviewed on 9 Nov 2026

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 NZ$252 per night from 11 Nov to 12 Nov
NZ$252
11 Nov - 12 Nov
includes taxes & fees
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.

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)
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
See properties

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$43
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$71
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

NZ$43
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
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 . 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.