North Side Vacation Packages
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Top North Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
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
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.
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.
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.
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.
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.
Ready to book your vacation to North Side?
North Side Hotel Deals
The Majestic Hotel
528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $211
CA $248 total
Sep 7 - Sep 8
includes taxes & fees
Hotel Lincoln
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
CA $210
CA $283 total
Sep 29 - Sep 30
includes taxes & fees
The Willows Hotel
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $234 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"The staff was extremely helpful and friendly. There weren’t amenities like a gym or pool, but the lobby was cute and cozy. They also served coffee all day with cookies at 4pm. The location was great for food, so many cafes and nice restaurants!"
Reviewed on Aug 28, 2026
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
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.
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!
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.
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.
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.
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.
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.
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 entertainment choices.
What to do in North Side
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
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 CA $1,280. 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
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- Downtown Chicago Vacations
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- Water Tower Place
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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.
