Near West Side Vacations from $341
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Your Near West Side Vacation
Organizing your next getaway just got a whole lot easier with a vacation package to Near West Side. Enjoy all this neighborhood has to offer while making nice memories you won't forget. When it's time to sightsee, you'll find lots of top attractions nearby including University of Illinois Chicago, United Center and Anna and Frederick Douglass Park. Visit one, two or more during your trip to Near West Side. Stop daydreaming and start doing. When you're ready to book your dream vacation to Near West Side, Expedia will help get you there.
The Latest Near West Side Vacation Packages
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Aug 7, 2026
Where to stay in Near West 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 West Side Hotel Deals
Holiday Inn & Suites Chicago - Downtown by IHG
"For the most part our stay was enjoyable and most of the staff was very polite and helpful. I didn’t give it 5 stars because the gentleman working the night shift was not only rude to my family but also rude to other people staying there. Also my husband and daughter said the pool water smelled weird ..."
Reviewed on Aug 7, 2026
Crowne Plaza Chicago West Loop by IHG
The Emily Hotel
"Proximity to good restaurants"
Reviewed on Aug 7, 2026
Stay near popular Near West Side attractions
United Center
University of Illinois Chicago
Credit Union 1 Arena
Union Park
Maxwell Street Market
The Old Post Office
City Winery
Thalia Hall
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
Explore a world of travel with Expedia
- Chicago Water Tower
- Marina City
- St. Basil Greek Orthodox Church
- Mary Bartelme Park
- Driehaus Museum
- Wrigley Field
- Crown Fountain
- Skydeck Ledge
- Harold Washington Library Center
- Goose Island Vacations
- Downtown Chicago Vacations
- West Loop Vacations
- Unity Temple
- Chicago Loop Synagogue
- Wicker Park Vacations
- Our Lady of Sorrows Basilica
- Grant Park
- Chicago Board of Trade Building
- Cadillac Palace Theatre
- Lincoln Park Conservatory
- Cna Center
- Canalport Riverwalk Park
- Marshall Field Building
- Montrose Beach
- Shops at North Bridge
- Gen. John Logan Memorial
- Michigan Avenue Bridge
- Chicago City Hall
- Holy Name Cathedral
- Tribune Tower
- 311 S Wacker Dr
- Monique Meloche Gallery
- Garfield Park Conservatory
- Magnificent Mile Vacations
- Film Row Cinema
- Columbia College Chicago
- Lincoln Park Zoo
- Packer Schopf Gallery
- Cooking & Hospitality Institute of Chicago
- Grace Abbott Homes Vacations
- Maggie Daley Park
- Monadnock Building
- Roosevelt University
- Art Institute of Chicago
- 333 West Wacker Drive
- Holy Trinity Russian Orthodox Cathedral
- Maxwell Street Market
- Rookery
- University of Illinois Chicago
- 900 North Michigan Shops
- Ping Tom Memorial Park
- Aon Center
- Northwestern Memorial Hospital
- Chase Tower
- Navy Pier
- American Police Center & Museum
- Chicago Museum Campus Vacations
- Buckingham Fountain
- Civic Opera House
- Jane Addams' Hull-House Museum
- Michigan Avenue
- The East Bank Club
- Chicago Children's Museum
- Millennium Park
- Picasso Statue
- Merchandise Mart
- Oak Street Beach
- Carbide and Carbon Building
- North Avenue Beach
- St. John Cantius Church
- Cibc Theatre
- Cloud Gate
- The Salt Shed
- Chicago Cultural Center
- Anna and Frederick Douglass Park
- Bally's Casino Chicago
- Ronald McDonald House near Lurie Children’s
- Robie House
- Garfield Park
- United Center
- St Nicholas Ukrainian Catholic Cathedral
- Fourth Presbyterian Church
- Auditorium Building and Theatre
- River North Vacations
- Richard Norton Gallery
- Richard J. Daley Center
- Goodman Theater
- Ohio Street Beach
- Wrigley Building
- Fisher Building
- Chicago Place Mall
- Daley Plaza
- Chicago History Museum
- Depaul University-Loop Campus
- House of Blues Chicago
- Water Tower Place
- Willis Tower
- The Loop Vacations
- Chicago Riverwalk
- Chicago Vacations