Near North Side Vacations from $266
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Your Near North Side Vacation
Your next escape beckons with a vacation package to Near North Side. Entertainment, relaxation and nonstop great times — you're sure to find it in this neighborhood. When it's time to get out and explore, you'll find a lot of popular attractions nearby including Millennium Park, Willis Tower and Art Institute of Chicago. Visit one, two or all during your trip to Near North Side. Stop dreaming and start doing. When you're ready to lock in your vacation to Near North Side, Expedia is here to help.
The Latest Near North Side Vacation Packages
theWit Chicago, a Hilton Hotel
Reviewed on Dec 19, 2025
The Emily Hotel
Reviewed on Dec 16, 2025
Where to stay in Near North Side
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Discover the most popular places to visit in Near North Side
Water Tower Place
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
875 North Michigan Avenue
You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Merchandise Mart
You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its fascinating museums.
Things to do
Chicago Bulls Basketball Game at United Center
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- Chicago Vacations
- Visit Downtown Chicago
- Dave & Buster's
- Annunciation Greek Orthodox Cathedral
- Newberry Library
- John Hancock Center
- Cooking & Hospitality Institute of Chicago
- Water Tower Place
- Holy Name Cathedral
- Rush Street Vacations
- Chicago Water Tower
- Navy Pier
- Aldo Castillo Gallery
- 900 North Michigan Shops
- Fourth Presbyterian Church
- Oak Street Beach
- Lookingglass Theatre
- Chinese Consulate
- Chicago Place Mall
- St. James Cathedral
- Magnificent Mile Vacations
- Driehaus Museum
- Broadway Playhouse
- River North Vacations
- Chicago History Museum
- Ann and Robert H. Lurie Children's Hospital
- Gold Coast Vacations
- Shops at North Bridge
- Northwestern Memorial Hospital
- Visit Rush Street
- American Medical Association Headquarters
- Cyrus McCormick Mansion
- Michigan Avenue
- Prentice Women's Hospital
- The East Bank Club
- Tribune Tower
- Streeterville Vacations
- Ohio Street Beach
- International Museum of Surgical Science
- Chicago Riverwalk
- Ronald McDonald House near Lurie Children’s
- Chicago Theatre
- Wrigley Building
- Richard Norton Gallery
- Museum of Broadcast Communications
- Marina City
- Merchandise Mart