
Old Town Chicago Holidays
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Your Old Town Chicago Holiday
Experience the best that Old Town Chicago has to offer with a tailor-made Old Town Chicago holiday package. From its cafes and bars and pubs to its history, you'll quickly fall for the charms of this commercial neighbourhood. When it's time to see the sights, you'll find lots of big-name attractions nearby including Wrigley Field, Millennium Park and Willis Tower. Tick off one, two or all during your trip to Old Town Chicago. Expedia will help turn your ideal Old Town Chicago holiday into reality, no matter your travel plans or budget.
Our guide on where to stay in Old Town Chicago

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.
Our pick of the best Old Town Chicago Hotel Deals

Congress Plaza Hotel
Reviewed on 13 Oct 2025

Freehand Chicago
Reviewed on 13 Oct 2025

Hilton Chicago/Magnificent Mile Suites
Reviewed on 13 Oct 2025
Frequently asked questions
Activities

Skydeck - Willis Tower Admission
