Oak Street

A coastal cityscape with high-rise buildings, a beach, and a river.
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was HK$6,405, price is now HK$4,530 per person
HK$4,530
per person
25 Nov - 28 Nov
found 15 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was HK$6,417, price is now HK$4,646 per person
HK$4,646
per person
25 Nov - 28 Nov
found 15 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
We had a good experience, nothing to complain!

Reviewed on 5 Oct 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was HK$6,049, price is now HK$4,715 per person
HK$4,715
per person
25 Nov - 28 Nov
found 15 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,346 reviews)

Tours & day trips

See all 258 activities
Architecture River Tour from Navy Pier

Architecture River Tour from Navy Pier

Activity duration is 1 hour
9.6 out of 10 with 1652 reviews
Free cancellation available
Price is HK$337 per adult
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Private & custom tours

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Chicago: Shooting & Spinning Art Experience (Neon Lights)

Chicago: Shooting & Spinning Art Experience (Neon Lights)

Activity duration is 45 minutes
Free cancellation available
Price is HK$895 per adult
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Food, drink & nightlife

See all 38 activities
City Cruises Chicago: Lake Michigan Premier Dinner Cruise

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Activity duration is 2 hours and 30 minutes
8.0 out of 10 with 44 reviews
Price is HK$1,243 per adult
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Classes & workshops

See all 27 activities
Chicago: BYOB Spray Paint and Sip Workshop

Chicago: BYOB Spray Paint and Sip Workshop

Activity duration is 1 hour and 30 minutes
10.0 out of 10 with 15 reviews
Free cancellation available
The previous price was HK$314 and current price is HK$283 per adult
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Attractions

See all 18 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 746 reviews
Free cancellation available
Price is HK$212 per adult
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Stay near popular Oak Street attractions

Oak Street

9.4/10 (3 reviews)
During your trip to Chicago, you can find the perfect gifts to bring home at Oak Street. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
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Top Oak Street Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The Chicago Hotel Collection - Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
River Hotel
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Eurostars Magnificent Mile
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
The Whitehall Hotel, BW Premier Collection
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
Warwick Allerton - Chicago
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
127 West Huron, at LaSalle Chicago IL
The Godfrey Hotel Chicago
See all 4,051 properties in Oak Street
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.