North Side Vacation Packages
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Top North Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
CA $1,301
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
En publicidad ofrecen uso de piscina en un entorno agradable familiar y fue lo contrario parejas en actos lasivos dentro de piscina y ninguna persona de servicio atentos a lo que pasa totalmente desagradable.
Reviewed on Aug 24, 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
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.
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.
Lake View East
While visiting Lake View East, you might make a stop by sights like Nettlehorst French Market and TimeLine Theatre.
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 $203
CA $239 total
Sep 9 - Sep 10
includes taxes & fees
Hotel Lincoln
1816 N Clark Street Chicago IL
CA $182
CA $249 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,163 reviews)
"The room I stayed in was disappointing. The wallpaper was peeling by the bed, the curtain stained, the bathroom frame popping off & the sliding bathroom door besides being filthy has a big gap so it doesn’t feel private in this little room. In the morning one of the other rooms was open for cleaning ..."
Reviewed on Aug 24, 2026
The Willows Hotel
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
CA $197
CA $231 total
Sep 7 - Sep 8
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 acclaimed art scene in this vibrant area.
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.
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.
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 $1,006. 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
- Visit Magnificent Mile
- Navy Pier
- Golf Vacations
- 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
- 875 North Michigan Avenue
- United Center
- Visit The Loop
- Wrigley Field
- The Loop Vacations
- Willis Tower
- Lincoln Park Zoo
- Ann and Robert H. Lurie Children's Hospital
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- Garfield Park Conservatory
- Art Institute of Chicago
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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.
