Oak Street
Visit Oak Street
Tours & day trips
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Architecture River Tour
Private & custom tours
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Sip Happens: Chicago Loop Prohibition Tour
![City centre Chicago City Tour In a Lamborghini[60 Minute Experience]](https://mediaim.expedia.com/localexpert/50806683/b6324a0b-7fb0-4936-8b5f-2fdebe79ae59.jpg?impolicy=resizecrop&rw=500&rh=280)
Food, drink & nightlife
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City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Attractions
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360 CHICAGO Observation Deck
Classes & workshops
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Chicago: BYOB Spray Paint and Sip Workshop
Popular places to visit
900 North Michigan Shops
You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.
875 North Michigan Avenue
You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Oak Street Beach
Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Chicago Water Tower
You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Water Tower Place
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
Holy Name Cathedral
After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Top Oak Street Hotel Deals
Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast
Four Seasons Hotel Chicago
Freehand Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.