North Side Vacations from $688
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The Latest North Side vacation packages
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 Holstein Park Public Pool, 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 Beat Kitchen and Martyrs', and you can jump on the metro at Addison Station (Brown Line) or Irving Park Station to get around the city.
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.
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 top-notch restaurants.
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 entertainment choices.
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 art scene 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.
What to do in North Side
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
North Side Hotel Deals
The Majestic Hotel
528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
$159 nightly
$187 total
Aug 10 - Aug 11
Total with taxes and fees
8.8/10 Excellent! (1,013 reviews)
"Excellent location to walk to Wrigley, however this hotel is a dump and outrageously overpriced."
Reviewed on Aug 6, 2026
Hotel Lincoln
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
$167 nightly
$196 total
Aug 30 - Aug 31
Total with taxes and fees
7.8/10 Good! (1,156 reviews)
"The hotel was great! Staff was incredibly attentive and kind. Would 100% stay again."
Reviewed on Aug 6, 2026
The Willows Hotel
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
$157 nightly
$185 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
"The staff was excited… Mia went out of her way to make us feel welcomed in Chicago"
Reviewed on Aug 7, 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.
Find the Best North Side Vacation Packages
North Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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- St Nicholas Ukrainian Catholic Cathedral
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- Chicago Place Mall
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- Navy Pier
- Water Tower Place
- Unity Temple
- Saint Joseph Hospital
- Elks Veterans Memorial
- Oak Street Beach
- Robie House
- Defiant Theatre
- Chicago Children's Museum
- 900 North Michigan Shops
- South Pond
- Vic Theatre
- Second City
- Amazing Chicago's Funhouse Maze
- Northalsted Vacations
- St. Josaphat Church
- Lighthouse ArtSpace Chicago
- Goose Island Vacations
- Baha'i House of Worship
- Marina City
- Riviera Theatre
- University of Illinois Chicago
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- Chicago Water Tower
- Magnificent Mile Vacations
- Henry Gerber House
- Briar Street Theatre
- Humboldt Park
- Depaul University-Lincoln Park
- Flat Iron Building
- Downtown Chicago Vacations
- Armitage Avenue
- Wrigley View Rooftop
- Cibc Theatre
- Advocate Illinois Masonic Medical Center
- Wrigley Building
- Lincoln Park Conservatory
- Farm-In-The-Zoo
- Cooking & Hospitality Institute of Chicago
- Monique Meloche Gallery
- North Avenue Beach
- Wicker Park Vacations
- Graceland Cemetery
- Ohio Street Beach
- Dave & Buster's
- Chicago Riverwalk
- Michigan Avenue
- Chicago Cultural Center
- Northwestern University
- Fourth Presbyterian Church
- Rookery
- Chicago Board of Trade Building
- Northwestern Memorial Hospital
- Lincoln Park Zoo
- Annunciation Greek Orthodox Cathedral
- Apollo Theater Chicago
- Carbide and Carbon Building
- St. Clements Church
- Our Lady of Lourdes Church
- Chicago Vacations
- Park West
- The Salt Shed
- St. John Cantius Church
- Richard J. Daley Center
- Cyrus McCormick Mansion
- Depaul Art Museum
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- Goodman Theater
- Tribune Tower
- Lincoln Park
- Buckingham Fountain
- Lakeview Vacations
- Cadillac Palace Theatre
- Marshall Field Building
- Daley Plaza
- Picasso Statue
- Depaul University-Loop Campus
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- Skydeck Ledge
- Driehaus Museum
- Art Institute of Chicago
- Chicago City Hall
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
