Near North Side Vacations from $341
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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
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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Near North Side Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
Holiday Inn Chicago Dwtn - The Mart by IHG
"Great stay! Would recommend."
Reviewed on Aug 7, 2026
The Chicago Hotel Collection - Magnificent Mile
"No coffee maker in room. Only every third day cleaning for the room. Phone did not work."
Reviewed on Aug 7, 2026
Stay near popular Near North Side attractions
Water Tower Place
875 North Michigan Avenue
Merchandise Mart
House of Blues Chicago
Tribune Tower
Ohio Street Beach
360 CHICAGO
Museum of Contemporary Art Chicago
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
Explore a world of travel with Expedia
- Cadillac Palace Theatre
- Chicago Loop Synagogue
- Aldo Castillo Gallery
- Lake Point Tower
- Grant Park
- United Center
- Richard Norton Gallery
- Downtown Chicago Vacations
- Ronald McDonald House near Lurie Children’s
- Magnificent Mile Vacations
- Crown Fountain
- Millennium Park
- Chicago City Hall
- Milton Lee Olive Park
- Harold Washington Library Center
- Chicago History Museum
- Amazing Chicago's Funhouse Maze
- House of Blues Chicago
- Willis Tower
- North Avenue Beach
- River North Vacations
- Goose Island Vacations
- Chicago Children's Museum
- Roosevelt University
- Merchandise Mart
- Shops at North Bridge
- The Loop Vacations
- Carbide and Carbon Building
- Marina City
- Chinese Consulate
- Chicago Riverwalk
- Chase Tower
- Fisher Building
- Richard J. Daley Center
- Driehaus Museum
- Lincoln Park Conservatory
- Robie House
- Aon Center
- Civic Opera House
- Montrose Beach
- Daley Plaza
- Fourth Presbyterian Church
- Marshall Field Building
- Museum of Contemporary Art Chicago
- Chicago Vacations
- Northwestern Memorial Hospital
- Michigan Avenue
- Gold Coast Vacations
- Michigan Avenue Bridge
- Henry Gerber House
- Ohio Street Beach
- Oak Street Beach
- The Salt Shed
- Ann and Robert H. Lurie Children's Hospital
- Bally's Casino Chicago
- Northwestern Pritzker School of Law
- Bridgehouse and Chicago River Museum
- Chicago Place Mall
- The East Bank Club
- St. James Cathedral
- Picasso Statue
- Skydeck Ledge
- 311 S Wacker Dr
- 875 North Michigan Avenue
- Art Institute of Chicago
- Chicago Board of Trade Building
- Second City
- 360 CHICAGO
- Cibc Theatre
- 333 West Wacker Drive
- International Museum of Surgical Science
- Maggie Daley Park
- Prentice Women's Hospital
- Farm-In-The-Zoo
- Rookery
- Cyrus McCormick Mansion
- Tribune Tower
- Goodman Theater
- Holy Name Cathedral
- Wrigley Field
- Wrigley Building
- Lighthouse ArtSpace Chicago
- Auditorium Building and Theatre
- Lincoln Park Zoo
- Chicago Water Tower
- Water Tower Place
- Cooking & Hospitality Institute of Chicago
- 900 North Michigan Shops
- Buckingham Fountain
- University of Illinois Chicago
- Dave & Buster's
- St. John Cantius Church
- Depaul University-Loop Campus
- Unity Temple
- Navy Pier
- Annunciation Greek Orthodox Cathedral
- Chicago Cultural Center
- Monadnock Building
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