Woodlawn Vacations from $408
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Woodlawn Vacation
From its cycling to its golfing and walking, there are tons of convincing reasons to book a vacation package to Woodlawn. When you're ready to escape the everyday, this green neighborhood is calling. Wondering what to see and do during your trip to Woodlawn? Nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Robie House are good places to begin. Expedia will help put your plans into action. Book your perfect Woodlawn vacation now.
The Latest Woodlawn Vacation Packages
Level Chicago – Old Town
Reviewed on Aug 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Aug 14, 2026
Where to stay in Woodlawn
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.
Lincoln Park
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.
Woodlawn Hotel Deals
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago
"Comfortable, cozy. We just didn't know that we couldn't use the pool or the oven"
Reviewed on Aug 14, 2026
Stay near popular Woodlawn attractions
Jackson Park
Obama Presidential Center
Rubenstein Forum
Bob-O-Link Meadow
Jackson Park Driving Range
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
Explore a world of travel with Expedia
- North Avenue Beach
- United Center
- Fisher Building
- Willis Tower
- Lakefront Trail
- Shops at North Bridge
- Jane Addams' Hull-House Museum
- Ohio Street Beach
- Marquette Building
- Depaul University-Loop Campus
- Driehaus Museum
- Santa Fe Building
- Film Row Cinema
- Roosevelt University
- Buckingham Fountain
- Robert W Roloson Houses
- The Salt Shed
- Downtown Chicago Vacations
- Cadillac Palace Theatre
- Chicago Vacations
- Holy Name Cathedral
- Lincoln Park Conservatory
- The Loop Vacations
- Old Colony Building
- Chicago Symphony Orchestra
- 900 North Michigan Shops
- Art Institute of Chicago
- Wrigley Building
- Rookery
- Chicago Place Mall
- Crown Fountain
- Hyde Park Vacations
- Obama's House
- Robie House
- Montrose Beach
- Carbide and Carbon Building
- Navy Pier
- Ping Tom Memorial Park
- Chicago Riverwalk
- Columbia College Chicago
- Elijah Muhammad House
- Tribune Tower
- Civic Opera House
- Grant Park
- Zhou B Art Center
- Gen. John Logan Memorial
- Canalport Riverwalk Park
- Chicago Cultural Center
- Chicago Children's Museum
- Chicago Loop Synagogue
- Water Tower Place
- Richard J. Daley Center
- Daley Plaza
- Mary Bartelme Park
- Chicago City Hall
- Lorado Taft's Midway Studios
- Symphony Center
- Picasso Statue
- Maxwell Street Market
- Skydeck Ledge
- University of Illinois Chicago
- Maggie Daley Park
- Midway Plaisance
- Marina City
- Goodman Theater
- Sr Crown Hall
- University of Chicago
- Burnham Park
- Bridgeport Art Center
- Mccormick Tribune Center
- Muddy Waters’ House
- Monadnock Building
- Wrigley Field
- South Loop Vacations
- Millennium Park
- American Police Center & Museum
- Auditorium Building and Theatre
- Chicago Architecture Foundation
- 311 S Wacker Dr
- Chicago Board of Trade Building
- South Commons Vacations
- Dusable Museum of African-American History
- Unity Temple
- Cna Center
- Chinatown Vacations
- Michigan Avenue
- Pontiac Building
- Lincoln Park Zoo
- Grace Abbott Homes Vacations
- Cibc Theatre
- Marshall Field Building
- Chicago Museum Campus Vacations
- Michigan Avenue Bridge
- 333 West Wacker Drive
- Magnificent Mile Vacations
- Merchandise Mart
- Griffin Museum of Science and Industry
- Chase Tower
- Ida B Wells House