Old Town Chicago

Chicago

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Photo by Marc Jacobs
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Photo by Rita Irvine

Popular places to visit

Things to do


Top hotels in Old Town Chicago

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
The price is S$228 per night from 1 Sept to 2 Sept
S$228
1 Sept - 2 Sept
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,218 reviews)
"Friendly"

Reviewed on 24 Aug, 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$283 per night from 14 Sept to 15 Sept
S$283
14 Sept - 15 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (9,016 reviews)
"I really enjoyed my stay here . The hotel is very historical and is known for hosting beautiful weddings, it’s huge , restaurants on property, and is very close to everything there is to see in downtown Chicago . Very close to the river walk , millennium park, coffee shops/breakfast, the loop , Taco ..."

Reviewed on 25 Aug, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is S$230 per night from 3 Sept to 4 Sept
S$230
3 Sept - 4 Sept
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,774 reviews)
"The staff were very accommodating and nice. The rooms were spacious and comfortable."

Reviewed on 24 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
The price is S$294 per night from 2 Sept to 3 Sept
S$294
2 Sept - 3 Sept
includes taxes & fees
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,882 reviews)
"Always love staying at The Palmer. The location is super convenient and the property oozes with Chicago charm. The staff is kind and always willing to help. Looking forward to my next stay."

Reviewed on 23 Aug, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
The price is S$216 per night from 2 Sept to 3 Sept
S$216
2 Sept - 3 Sept
includes taxes & fees
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (3,749 reviews)
"X"

Reviewed on 24 Aug, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is S$155 per night from 3 Sept to 4 Sept
S$155
3 Sept - 4 Sept
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,234 reviews)
"I liked that it was walking distance to a lot of the places I went to in downtown"

Reviewed on 23 Aug, 2025

Freehand 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.

Other neighbourhoods around Old Town Chicago

Chicago which includes a city and modern architecture

Lincoln Park

5/5(5 area reviews)

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Lincoln Park
Gold Coast showing street scenes as well as a couple

Gold Coast

The ample dining options and fantastic lake views are top of the list for many visitors to Gold Coast. A stop by Michigan Avenue or Lake Michigan might round out your trip.

Gold Coast
Magnificent Mile - River North featuring street scenes, night scenes and signage

Near North Side

4.5/5(248 area reviews)

Known for its fascinating museums, panoramic lake views and popular shops, there's plenty to explore in Near North Side. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at Clark-Division Station or Chicago Station (Brown Line) to see more of the city.

Near North Side
Default Image

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

River North
Magnificent Mile - River North

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

Magnificent Mile
Navy Pier which includes general coastal views and wild flowers as well as a couple

Streeterville

Michigan Avenue and Navy Pier are just a few worthwhile attractions to visit in Streeterville. Travellers also love the fascinating museums, panoramic lake views and popular shops.

Streeterville

Old Town Chicago