Old Town Chicago, IL

Chicago

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Photo by Marc Jacobs
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Popular places to visit


Old Town Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
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! (9,294 reviews)
"Location is perfect. Would definetly stay here again on my next trip to Chicago"

Reviewed on 24 September 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is AED 590 per night from Oct 20 to Oct 21
AED 590
AED 693 total
20 Oct - 21 Oct
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,935 reviews)
"Great hotel. Gret spot close to everything. Great staff."

Reviewed on 22 September 2025

Hilton Chicago/Magnificent Mile Suites
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 AED 661 per night from Oct 2 to Oct 3
AED 661
AED 776 total
2 Oct - 3 Oct
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! (3,958 reviews)
"Very good hotel"

Reviewed on 23 September 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
The price is AED 745 per night from Oct 25 to Oct 26
AED 745
AED 874 total
25 Oct - 26 Oct
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (2,139 reviews)
"Great"

Reviewed on 19 September 2025

Hilton Chicago O'Hare Airport
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 668 per night from Sep 28 to Sep 29
AED 668
AED 784 total
28 Sep - 29 Sep
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,813 reviews)
"Please try to restock luggage tag bands"

Reviewed on 17 September 2025

citizenM Chicago Downtown
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is AED 387 per night from Oct 20 to Oct 21
AED 387
AED 519 total
20 Oct - 21 Oct
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! (2,373 reviews)
"The hotel was beautiful and unique, and the staff were friendly! We enjoyed the cocktail lounge on the first floor. My only complaint is that our Air Conditioning unit didn’t work, but we also didn’t bring that to the attention of the front desk because we had reservations somewhere and weren’t back ..."

Reviewed on 23 September 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 neighborhoods around Old Town Chicago

Chicago which includes modern architecture and a city

Lincoln Park

4.5/5(320 area reviews)

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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

Gold Coast

The abundant dining options and 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 showing night scenes, a city and signage

Near North Side

4.5/5(12,034 area reviews)

Michigan Avenue and Navy Pier are a few top attractions in Near North Side. Hop around the city on the metro at Clark-Division Station or Chicago Station (Brown Line) and check out the area's fascinating museums, panoramic lake views, and popular shops.

Near North Side
River North showing railway items, street scenes and a city

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

River North
Magnificent Mile - River North

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Magnificent Mile
Navy Pier featuring general coastal views and wildflowers as well as a couple

Streeterville

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

Streeterville


Old Town Chicago, IL

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