Old Town Triangle Vacations from $345
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Your Old Town Triangle Vacation
Whatever your travel style, you can discover it all with a personalized Old Town Triangle vacation package. Spend your next escape uncovering this neighborhood's history and its other charms. Some top nearby attractions to visit during your trip to Old Town Triangle include Wrigley Field, Millennium Park and Willis Tower. Expedia can help turn your ideal Old Town Triangle vacation into reality, no matter your travel plans or budget.
The Latest Old Town Triangle Vacation Packages
Hotel Riu Plaza Chicago
Reviewed on Aug 6, 2026
Where to stay in Old Town Triangle
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).
Old Town Triangle Hotel Deals
Congress Plaza Hotel
"Room was clean, place is definitely dated. Workers were nice but it advertised that you could get discounts for Shedd aquarium tickets and they told us no. That was a slight bummer. The bed was really uncomfortable. I’m usually not too picky about the beds my shoulders and neck have been in pain ..."
Reviewed on Aug 6, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"Clean room and great staff"
Reviewed on Aug 6, 2026
Hilton Chicago O'Hare Airport
"Comfortable hotel in the airport. Staff is friendly and professional. Restaurant and bar were super congenial. Great place to stay on a quick trip to Chicago or on layover."
Reviewed on Aug 6, 2026
Stay near popular Old Town Triangle attractions
Chicago History Museum
Park West
Second City
Midwest Buddhist Temple
Henry Gerber House
Hudson Chess Park
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
