North Side Holidays

Photo by Vincent Ramundo

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Top Flight + Hotel Deals in North Side

Price found within the past 48 hours. Click for updated prices.
Cambridge Inn on Main

Cambridge Inn on Main

€2,708
per person
17 Dec - 21 Dec
found 19 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (74 reviews)
Everything about this hotel was great! A very historic Boutique Hotel that takes you back in time! Each room has a theme of its own which is unique to the period. The owner was very friendly and made sure that I had everything that I needed to make my stay excellent! If you're ever in that area or even doing business in the Madison Wisconsin area you may consider taking an extra half hour to drive to this hotel and stay there. I don't think you'll be disappointed at all as a matter of fact I would be surprised if you didn't like it. I've been in hotels halfway around the world and I must say that next time I'm back in that area I will be staying here!

Reviewed on 4 Oct 2026

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 wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

6 out of top 10 points of interest in this area

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

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A cityscape with a dense urban area, a prominent train track, and a distant skyline of tall buildings.

Logan Square

The breweries and live music are just a few things visitors like about Logan Square. Concord Music Hall and Milwaukee Avenue are worthwhile spots to check out, and you can hop on the metro at Logan Square Station or California Station (Blue Line) to get around the larger area.

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A baseball stadium filled with spectators during a game.

Wrigleyville

You might enjoy the bars while in Wrigleyville. Wrigley Field is a notable sight, and you can get around town at Sheridan Station or Addison Station (Red Line) to see more of the city.

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A pedestrian bridge with a cyclist, people walking, and buildings in the background.

Bucktown

Well liked for its churches and architecture, Bucktown is worth a visit. Check out the variety of things to see and do like Milwaukee Avenue and Riverfront Plaza, and jump on the metro at Western Station (O Hare Branch) to get around the city.

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A cityscape with a river, high-rise buildings, and a marina.

Avondale

Check out the restaurants during your time in Avondale. Hop around the Chicago area on the metro at Belmont Station (Blue Line) to see top sights like Milwaukee Avenue and Sleeping Village.

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Top hotels in North Side

Hotel Lincoln

Hotel Lincoln

1816 N Clark Street Chicago IL
€173
25 Oct - 26 Oct
includes taxes & fees
Hotel Lincoln
The Majestic Hotel

The Majestic Hotel

528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
€159
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (1,024 reviews)
"I don't know why this hotel has such high ratings. It is really run down. The photos on the website are deceptive. It is in a very nice neighborhood, but it's not nearly as close to Wrigley Field as they make it seem."

Reviewed on 5 Oct 2026

The Majestic Hotel
The Willows Hotel

The Willows Hotel

555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
€125
26 Oct - 27 Oct
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"A great place to stay and a very handy location for walking to many things."

Reviewed on 4 Oct 2026

The Willows Hotel
See all 536 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

Wrigley Field

9.0/10 (11,704 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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A sign for the Pritzker Family Children's Zoo surrounded by autumn foliage.

Lincoln Park Zoo

9.0/10 (1,096 reviews)
This small zoo in the center of Chicago is perfect for small children and parents looking for a quiet, leisurely stroll — and some impressive animals!
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A vintage car in a museum exhibit, a neon sign reading "GAS FOR LESS", and a historical mural on the wall.

Chicago History Museum

9.0/10 (37 reviews)
Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.
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A cityscape with a prominent clock tower, a mix of modern and historic buildings, and a dense skyline.

Park West

8.8/10 (12 reviews)
You can enjoy a show at Park West on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
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Vic Theatre

You can make plans for a show at Vic Theatre during your stay in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
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Theater Wit

You can get tickets for a performance at Theater Wit during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
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Second City

9.6/10 (15 reviews)
You can make plans for a show at Second City on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
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Lincoln Hall

You can get tickets for a performance at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
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What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

€24
per adult
98% of travellers recommend
Flyover in Chicago
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 €2,708. 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.

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