Old Town Chicago, IL

Chicago

A street with outdoor seating, brick buildings, and signs for a barbershop and a restaurant.
A cityscape with a mix of modern and historic architecture, including a prominent red brick building with a green awning and a tall skyscraper in the background.
A wrought iron sign with the inscription 'OLD TOWN' mounted on a building facade.
A black SUV parked in front of a building with red umbrellas and a sign that reads 'Woodie's Flat.'
A mural on a brick building with a sign for 'Corcoran's Grill & Pub' and 'Old Town.'

Stay near popular Old Town Chicago attractions

Second City

9.6/10 (15 reviews)
You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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Old Town Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ₩233,495 per night from Sep 27 to Sep 28
₩233,495
₩277,599 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,204 reviews)
"My stay was great. But the hallway was off putting."

Reviewed on Sep 10, 2026

Congress Plaza Hotel
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 price is ₩239,820 per night from Sep 21 to Sep 22
₩239,820
₩285,124 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
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Kasa Magnificent Mile Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is ₩224,048 per night from Sep 27 to Sep 28
₩224,048
₩266,372 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
The price is ₩272,221 per night from Sep 20 to Sep 21
₩272,221
₩323,642 total
Sep 20 - Sep 21
includes taxes & fees
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,594 reviews)
"Didn’t advertise the pool was not functioning pictures of pool in advertisements deceiving and elevator took 20 minutes minimum to go down many people had to walk 22 plus flights of stairs vs wait for no elevator to stop on high floors. Won’t stay there again"

Reviewed on Sep 10, 2026

Hampton Inn Chicago Downtown/Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is ₩304,502 per night from Sep 25 to Sep 26
₩304,502
₩401,351 total
Sep 25 - Sep 26
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,171 reviews)
"nice"

Reviewed on Sep 10, 2026

Hilton Chicago
See all 4,474 properties in Old Town 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.

Where to stay in Old Town Chicago

Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most.
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops, and acclaimed art galleries.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

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.

Old Town Chicago, IL