TOP Hotels with Entertainment in Old Town Chicago, IL for 2026

A coastal cityscape with a marina, high-rise buildings, and a river.

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Top Old Town Chicago Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Room was clean. Beds comfortable. Staff was kind and responsive. Parking was very expensive ($88 a night)."

Hilton Chicago

8/10 Good

"Waited a long time to check in. Loved the games in the lobby! Pool was great! Housekeeping didn’t clean our room on the second night- we came back to a dirty room with no sheets in a bed and the do not disturb sign was on the door. I called the front desk, but no one came so then I had to go track someone down in the hallway. We ended up waiting up at night to have someone come out sheets on the bed so we could go to sleep."

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Top Old Town Chicago Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

The Allegro Royal Sonesta Hotel Chicago Loop

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection - Magnificent Mile

Holiday Inn & Suites Chicago - Downtown by IHG

Hyatt Regency McCormick Place Chicago

Crowne Plaza Chicago West Loop by IHG

Hyatt Regency Chicago

Hilton Chicago

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Search Hotels with Entertainment in Old Town Chicago

Change your mind

Treat yourself

Be picky

Check availability on Old Town Chicago Hotels with Entertainment

Top Old Town Chicago Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

Explore a world of travel with Expedia