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 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 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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Find the Best North Side Vacation Packages

North Side Hotel Deals

Hotel Lincoln

Hotel Lincoln

1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
NT$5,137
NT$6,859 total
Oct 25 - Oct 26
includes taxes & fees
8/10 Very Good! (1,155 reviews)
"What a cute little kitschy hotel. I prefer to stay in boutique hotels when travelling. This was a cute little hotel with a beautiful rooftop and within walking distance to everything I needed."

Reviewed on 2026/9/30

Hotel Lincoln
The Majestic Hotel

The Majestic Hotel

528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
NT$7,292
NT$8,561 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (1,031 reviews)
"The property has so much old school Chicago charm! I loved my stay here. It was comfortable and I had everything I needed. Plus, the location was central to everything. I stayed here in order to see shows at the Metro and had a nice, safe walk back from the venue at night with my friends. The front ..."

Reviewed on 2026/9/30

The Majestic Hotel
The Willows Hotel

The Willows Hotel

555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
NT$6,170
NT$7,243 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (1,020 reviews)
"This was my first time staying here at The Willow Hotel. It’s an older building, but very clean. Eric, the day employee, was truly amazing. Very nice and helpful. I booked an executive king room. It was very spacious, the bed and pillows were very comfortable. The mini fridge was fully stocked with ..."

Reviewed on 2026/9/29

The Willows Hotel
See all 553 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 make plans for a show at Park West during your stay in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
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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 acclaimed theater scene in this vibrant area.
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Second City

9.6/10 (15 reviews)
You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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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 art 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.