Chicago Oak Street Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Nov - 3 Nov
Tomorrow
3 Nov - 4 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Oak Street

Front of property – evening/night
The Peninsula Chicago
The Peninsula Chicago
5.0 star property
9.8 out of 10, Exceptional, (1025)
"Fantastic hotel "
United States
Jennifer
The price is HK$4,468
HK$5,245 total
includes taxes & fees
16 Nov - 17 Nov
The Peninsula Chicago
Lobby
The Langham, Chicago
The Langham, Chicago
5.0 star property
9.8 out of 10, Exceptional, (1018)
"Excellent stay"
United States
KEDARNATH
The price is HK$3,887
HK$4,563 total
includes taxes & fees
23 Nov - 24 Nov
The Langham, Chicago
1 bedroom, premium bedding, down duvets, pillow-top beds
Park Hyatt Chicago
Park Hyatt Chicago
5.0 star property
9.6 out of 10, Exceptional, (1000)
"beautiful room and hotel great bar!"
United States
ravi
The price is HK$3,846
HK$4,515 total
includes taxes & fees
23 Nov - 24 Nov
Park Hyatt Chicago
Aerial view
Residence Inn Chicago Downtown Magnificent Mile
Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
9.6 out of 10, Exceptional, (378)
"Clean an a very friendly and helpful staff "
United States
Kevin
The price is HK$1,049
HK$1,231 total
includes taxes & fees
23 Nov - 24 Nov
Residence Inn Chicago Downtown Magnificent Mile
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (174)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Bar (on property)
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 star property
9.4 out of 10, Exceptional, (2209)
"Perfect Chicago location …have stayed here quite a few times and always great!"
United States
Diane
The price is HK$1,462
HK$1,944 total
includes taxes & fees
23 Nov - 24 Nov
Sofitel Chicago Magnificent Mile
Interior
Viceroy Chicago
Viceroy Chicago
4.5 star property
9.4 out of 10, Exceptional, (1123)
"Great location, clean, modern, good food/drink, friendly staff. "
United States
Katie
The price is HK$1,904
HK$2,463 total
includes taxes & fees
23 Nov - 24 Nov
Viceroy Chicago
Exterior
Waldorf Astoria Chicago
Waldorf Astoria Chicago
5.0 star property
9.4 out of 10, Exceptional, (1001)
"This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. "
United States
william
The price is HK$3,664
HK$4,301 total
includes taxes & fees
23 Nov - 24 Nov
Waldorf Astoria Chicago
Front of property
The Talbott, Autograph Collection
The Talbott, Autograph Collection
4.5 star property
9.4 out of 10, Exceptional, (42)
"The boutique hotel had some cute features to it; beautiful bathroom, nice little restaurant, all very small and quaint. "
United States
Dawne
The price is HK$1,116
HK$1,505 total
includes taxes & fees
23 Nov - 24 Nov
The Talbott, Autograph Collection
Reception
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
5.0 star property
9.4 out of 10, Exceptional, (999)
"Amazing hotel"
United States
David
The price is HK$3,807
HK$4,470 total
includes taxes & fees
24 Nov - 25 Nov
Four Seasons Hotel Chicago
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2701)
"Great place to stay "
United States
Larry William
The price is HK$879
HK$1,251 total
includes taxes & fees
25 Nov - 26 Nov
Hotel Riu Plaza Chicago
Restaurant
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 star property
9.2 out of 10, Wonderful, (1255)
"fun place to stay for a weekend getaway!"
United States
Robyn
The price is HK$1,041
HK$1,451 total
includes taxes & fees
23 Nov - 24 Nov
Thompson Chicago, by Hyatt
Lobby
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
9.4 out of 10, Exceptional, (3370)
"Great location "
United States
Shella
The price is HK$1,222
HK$1,434 total
includes taxes & fees
24 Nov - 25 Nov
LondonHouse Chicago, Curio Collection by Hilton
In-room safe, desk, laptop workspace, blackout curtains
Aloft Chicago Downtown River North
Aloft Chicago Downtown River North
3.5 star property
9.4 out of 10, Exceptional, (1169)
"Great stay in a great location. "
United States
Sage
The price is HK$932
HK$1,095 total
includes taxes & fees
24 Nov - 25 Nov
Aloft Chicago Downtown River North
Exterior
Moxy Chicago Downtown
Moxy Chicago Downtown
3.0 star property
9.4 out of 10, Exceptional, (834)
"Great place to stay"
United States
Mason
The price is HK$874
HK$1,026 total
includes taxes & fees
23 Nov - 24 Nov
Moxy Chicago Downtown
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (4044)
"Great stay"
United States
Riley
The price is HK$885
HK$1,039 total
includes taxes & fees
19 Nov - 20 Nov
citizenM Chicago Downtown
Exterior
Loews Chicago Hotel
Loews Chicago Hotel
4.5 star property
9.4 out of 10, Exceptional, (1590)
"Very nice, great location, staff was easy to talk to/message for accommodations"
United States
Judith
The price is HK$1,391
HK$1,879 total
includes taxes & fees
24 Nov - 25 Nov
Loews Chicago Hotel
Bar (on property)
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
5.0 star property
9.4 out of 10, Exceptional, (1759)
"Very clean very nice hotel. Easy accesss to restaurants and shopping. "
United States
Melvin
The price is HK$3,351
HK$3,934 total
includes taxes & fees
9 Nov - 10 Nov
Trump International Hotel & Tower Chicago
Daily full breakfast for a fee
Hotel EMC2, Autograph Collection
Hotel EMC2, Autograph Collection
4.0 star property
9.4 out of 10, Exceptional, (1000)
"Solid choice in Chicago with very nice staff!"
United States
Susann
The price is HK$1,321
HK$1,551 total
includes taxes & fees
23 Nov - 24 Nov
Hotel EMC2, Autograph Collection
2 bars/lounges
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 star property
9.4 out of 10, Exceptional, (3381)
"Great place to stay "
United States
Mariana Meza
The price is HK$1,119
HK$1,542 total
includes taxes & fees
24 Nov - 25 Nov
Hyatt Regency Chicago
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.
View all properties

Hotels close to Oak Street with free breakfast

Lobby
The Langham, Chicago
The Langham, Chicago
5.0 star property
  • Breakfast included
9.8 out of 10, Exceptional, (1018)
The price is HK$3,887
HK$4,563 total
includes taxes & fees
23 Nov - 24 Nov
The Langham, Chicago
See more properties

Hotels close to Oak Street with a pool

Front of property – evening/night
The Peninsula Chicago
The Peninsula Chicago
5.0 star property
  • Pool
9.8 out of 10, Exceptional, (1025)
The price is HK$4,468
HK$5,245 total
includes taxes & fees
16 Nov - 17 Nov
The Peninsula Chicago
See more properties

Top guest rated hotels close to Oak Street

Restaurant
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 star property
    9.2 out of 10, Wonderful, (1255)
    The price is HK$1,041
    HK$1,451 total
    includes taxes & fees
    23 Nov - 24 Nov
    Thompson Chicago, by Hyatt
    See more properties

    Top Oak Street Hotel Reviews

    Embassy Suites by Hilton Chicago Downtown River North

    Embassy Suites by Hilton Chicago Downtown River North

    10/10 Excellent
    "Amazing amenities, cleanness and quite space"
    Serra 3-night trip
    Posted 1 day ago
    Embassy Suites by Hilton Chicago Downtown River North

    Hotels near other Oak Street attractions

    At Bloomingdales, great place to shop and eat. 🎄
    Photo by Rita Irvine
    Open Photo by Rita Irvine

    900 North Michigan Shops

    You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
    See properties
    John Hancock Centre, Chicago, Illinois, USA

    875 North Michigan Avenue

    4.5/5 (2,896 reviews)
    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 fascinating museums.
    See properties

    Frequently asked questions

    What's the area like around Oak Street?
    Oak Street is located in Chicago. This metropolitan area is known for its stunning architecture and top museums. If you're looking for a convenient place to stay, take a look at the 759 hotels and other accommodation options you'll find within a mile.
    What's the best place to stay close to Oak Street?
    Adjacent to Oak Street, Hilton Chicago/Magnificent Mile Suites is one of the top choices for your stay based on our traveller data, and this hotel offers a fitness centre and valet parking. Other good choices close by include The Whitehall Hotel, BW Premier Collection and Freehand Chicago.
    How many hotels will I be able to find close to Oak Street?
    Expedia has 759 hotels and other accommodation options within a mile from Oak Street.
    If I need to cancel the hotel reservation for my stay near Oak Street, will I receive a refund?
    Yes! Most hotel reservations are refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to view the best deals available near Oak Street.
    What can I see and do near Oak Street?
    You might want to spend some time browsing the exhibits at Museum of Contemporary Art Chicago, International Museum of Surgical Science or Chicago History Museum. Chicago Water Tower, Holy Name Cathedral and Tribune Tower are some of the local landmarks to explore. You can watch performances at Broadway Playhouse, Second City and House of Blues Chicago if you're interested in local theatre.
    How can I get to Oak Street?
    With so many transport options, seeing the area around Oak Street is simple. Take advantage of metro transport at State Station, Clark-Lake Station and Lake Station. If you want to journey outside of the area, jump aboard a train from Millennium Station, Chicago Van Buren Street Station or Chicago Union Station.

    Explore a world of travel with Expedia