Old Town Chicago

Chicago

Old Town Chicago Neighborhood entrance gate and sign
Old Town Chicago Neighborhood entrance gate and sign

Popular places to visit

Things to do


Top hotels in Old Town Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is S$282 per night from 13 Mar to 14 Mar
S$282
13 Mar - 14 Mar
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (9,881 reviews)
Great location, beautiful historic hotel with clean, updated rooms.

Reviewed on 11 Feb, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is S$203 per night from 4 Mar to 5 Mar
S$203
4 Mar - 5 Mar
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free Wi-Fi and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk ...
9.2/10 Wonderful! (3,333 reviews)
Excellent

Reviewed on 13 Feb, 2026

Hotel Riu Plaza Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is S$243 per night from 27 Feb to 28 Feb
S$243
27 Feb - 28 Feb
includes taxes & fees
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,634 reviews)
Staff was courteous and our lake view room was great. Kids enjoyed the pool.

Reviewed on 16 Feb, 2026

Hilton Chicago
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$140 per night from 22 Feb to 23 Feb
S$140
22 Feb - 23 Feb
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service and a fitness centre. Our guests praise the breakfast and the pool in their reviews. Popular ...
8.4/10 Very Good! (5,674 reviews)
The clean rooms and the staff was excellent.

Reviewed on 16 Feb, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is S$291 per night from 14 Mar to 15 Mar
S$291
14 Mar - 15 Mar
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.2/10 Very Good! (2,202 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on 9 Feb, 2026

Hilton Chicago O'Hare Airport
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is S$154 per night from 28 Feb to 1 Mar
S$154
28 Feb - 1 Mar
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy a fitness centre, valet parking (surcharge) and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (3,798 reviews)
Perfect location on the Magnificent Mile! Love the coziness and clean beautiful comfortable room!

Reviewed on 15 Feb, 2026

Hilton Chicago/Magnificent Mile Suites
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.

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Other neighbourhoods around Old Town Chicago

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
Chicago_NearNorthSide_137043_09

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
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
River North showing railway items, street scenes and a city

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