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

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
Lincoln Park

Lincoln Park

7 out of top 10 points of interest in this area
5/5(4 area reviews)

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

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$372 per night from 6 July to 7 July
NZ$372
6 July - 7 July
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"The location of the WIllows Hotel is fantastic. It is in a vibrant part of Chicago, near the lake with many restaurants and cafes and businesses nearby. The staff were very friendly and helpful. The property itself, while charming and old, is also very tired and is in need of renovations to justify ..."

Reviewed on 25 June 2026

The Willows Hotel
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$354 per night from 8 July to 9 July
NZ$354
8 July - 9 July
includes taxes & fees
7.8/10 Good! (1,134 reviews)
"The room did not look like the photos used online- later found that the photos used were of newly renovated rooms in the building. Theirs is no parking like it claims as well, had to park on the street and pay for street parking and it was terrifying as a female alone walking back from my car at ..."

Reviewed on 25 June 2026

Hotel Lincoln
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$377 per night from 8 July to 9 July
NZ$377
8 July - 9 July
includes taxes & fees
7/10 Good! (1,002 reviews)
"Perfect location to Wrigley."

Reviewed on 24 June 2026

The Chicago Hotel Collection - Wrigleyville
See all 557 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

Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/5 (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$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$68
per adult
92% of travellers recommend
Art Institute of Chicago
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in North Side

Frequently asked questions

Can I cancel my flight booking to North Side due to COVID-19?
In these difficult times, many carriers are offering more flexibility. Head to our Customer Service Portal for details about cancelling or amending your flight due to COVID-19.
What's the best way to find cheap flights to North Side that have flexible change policies?
We understand that travel schedules can change in the blink of an eye, so choosing a flexible fare with Expedia is a wise idea. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to North Side is only a few clicks away.
What are some of the general tips for travellers to North Side during the COVID-19 outbreak?
With new COVID-19 safety measures to follow, travel looks a bit different in this day and age. Here are a few things to know before you hop on that plane to North Side:
  • Investigate if any restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so don't forget to check government advisories before booking.
  • When you go through airport screening, keep your face mask on. You will be asked to lower it briefly for ID purposes. Anyone refusing to wear a mask may be denied entry or boarding.
  • Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. After that, hold it up for inspection.
  • You are now permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. You'll need to remove it for X-ray screening.
  • Remove personal items from your pockets, like your phone, keys and wallet, and put them in your carry-on instead of into bins. This will minimize handling during screening.
  • Separate any food you have for X-ray screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to North Side?
Let American Airlines take you there. This popular carrier provides 13307 flights a month to O'Hare Intl. Airport (ORD), a North Side gateway.
How can I find cheap tickets to North Side?
An effective strategy for nabbing cheap airfares is to be flexible with your dates. Begin with searching for your flight to North Side, then click on the "flexible dates" box for a list of prices for nearby days. Another helpful hint? Book in advance. To give you an idea of fares, was the best price for a flight to North Side in the last seven days.
How much is a flight to North Side?
One-way flights departing from () sold for as little as in the last seven days. During this period, the cost of a return airfare to North Side ranged between and . If you spot a good deal, book fast — these fares don't hang around.
What are the most popular airports to fly into in North Side?
North Side's primary gateway is O'Hare Intl. Airport (ORD). Get your exciting journey underway by locking in a seat on one of the 33491 flights a month to this destination.
When is the cheapest time to fly to North Side?
If you can be flexible with your travel dates to North Side, depart early in the week. The most affordable day to take off is usually Tuesday, closely followed by Monday. Saturday is typically the costliest day, with many holiday makers preferring to fly on the weekend.
How much is a plane ticket to North Side?
Airfares to North Side varied from to in the last seven days. Generally, the quicker you book the better the deal.
Which airlines with flights to North Side employ COVID-19 cleanliness policies?
As travel borders start to open, most airlines have resumed services with new strategies including social distancing and staggered boarding and disembarkation. Here's what a number of carriers are doing to ease the spread of COVID-19:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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.