North Side Vacations

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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

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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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.

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

Logan Square

Get to know Logan Square and its many features like its breweries and live music. You might want to explore sights like Concord Music Hall and Milwaukee Avenue, and you can jump on the metro at Logan Square Station or California Station (Blue Line) to get around 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 Holstein Park Public Pool, and jump on the metro at Western Station (O Hare Branch) to get around the city.

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A city skyline at sunset with a snow-covered park in the foreground.

North Center

Get to know North Center and its many features like its bars and live music. You might want to explore sights like Martyrs' and Beat Kitchen, and you can jump on the metro at Addison Station (Brown Line) or Irving Park Station to get around the city.

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Find the Best North Side Vacation Packages

North Side Hotel Deals

The Majestic Hotel

The Majestic Hotel

528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
NT$4,428
NT$5,199 total
Aug 24 - Aug 25
includes taxes & fees
The Majestic Hotel
Hotel Lincoln

Hotel Lincoln

1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
NT$4,325
NT$5,909 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (1,155 reviews)
"The rooms are so busted. No hot water,very low water pressure , peeling wallpaper, dusty Ac, rusted bath lights, cracking ceiling, cheap furniture, mattress so old u can feel the springs, old tv that barely worked , dirty accent chair, weird curtains that barely closed and attached to wall by a hook ..."

Reviewed on 2026/8/15

Hotel Lincoln
The Willows Hotel

The Willows Hotel

555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
NT$3,644
NT$4,278 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Good"

Reviewed on 2026/8/15

The Willows Hotel
See all 519 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 red barn with a white door, surrounded by a garden with various plants and flowers.

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 make plans for a show at Park West during your stay in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
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Armitage Avenue

During your trip to Chicago, you can do some window-shopping at Armitage Avenue. Stroll along the lakeside in this vibrant area, or check out its lively bars.
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Vic Theatre

You can get tickets for a performance at Vic Theatre during your trip to Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
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Theater Wit

You can make plans for a show at Theater Wit during your stay in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.
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Lincoln Hall

You can enjoy a show at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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Frequently asked questions

How much does a North Side vacation package cost?
We make it simple to travel the world, with North Side vacation packages starting from just . You'll have the flexibility to bundle your favorite 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 vacation 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 vacation?
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, cozy city apartments and even houseboats and castles!
Can I choose my airline with a North Side Expedia vacation 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 vacation package?
You can. We realize life happens, so we're here to help if you need to make changes to your North Side vacation 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.