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.
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.
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.
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.
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.
Ready to book your vacation to North Side?
North Side Hotel Deals
Hotel Lincoln
1816 N Clark Street Chicago IL
CA $192
CA $262 total
Nov 9 - Nov 10
includes taxes & fees
8/10 Very good! (1,153 reviews)
"Right from the beginning we had problem with check in. Because the reservation was made via Expedia they had issue with checking us in. I had to show the proof of payment and proof of reservation . Then in the morning we have noticed that we haven't receive a Lake View Room as we ordered. I had mentioned ..."
Reviewed on Oct 6, 2026
The Majestic Hotel
528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $195
CA $228 total
Nov 8 - Nov 9
includes taxes & fees
8.8/10 Excellent! (1,022 reviews)
"Nice historical building in quiet Lakeview. Chicago Cubs theme throughout. Solid place to stay. I didn't give it all 5's because this place is old and unless it is gut renovated, it won't have that clean, look and feel of a newer building. The staff were friendly. Our room was large with a separate ..."
Reviewed on Oct 6, 2026
The Willows Hotel
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
CA $171
CA $201 total
Nov 1 - Nov 2
includes taxes & fees
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 fascinating museums in this vibrant area.
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 acclaimed theater scene.
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.
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.
What to do in North Side
Skydeck Chicago at Willis Tower
CA $59
per adult
88% 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 $692. 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.
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- Downtown Chicago Vacations
- Visit Magnificent Mile
- Navy Pier
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- Unity Temple
- Buckingham Fountain
- Millennium Park
- Marina City
- Water Tower Place
- International Museum of Surgical Science
- Grant Park
- Northwestern University
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- Frank Lloyd Wright Historic District
- Chicago Theatre
- Robie House
- Griffin Museum of Science and Industry
- Ernest Hemingway Museum and House
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- The Loop Vacations
- Willis Tower
- Lincoln Park Zoo
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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.
