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
Fully refundable
The price is ₩153,611 per night from Nov 10 to Nov 11
₩153,611
₩182,627 total
Nov 10 - Nov 11
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 ...
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 ₩160,803 per night from Nov 22 to Nov 23
₩160,803
₩191,179 total
Nov 22 - Nov 23
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 ...
8/10 Very Good! (2,601 reviews)
"Beautiful hotel, dated rooms."

Reviewed on Oct 26, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is ₩153,478 per night from Nov 23 to Nov 24
₩153,478
₩182,472 total
Nov 23 - Nov 24
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 ...
8.8/10 Excellent! (5,573 reviews)
"Room was clean at check-in, and cleaned daily by the staff. Plenty to do nearby, can walk just about anywhere."

Reviewed on Oct 26, 2026

River Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
The price is ₩157,448 per night from Nov 23 to Nov 24
₩157,448
₩187,187 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ₩159,529 per night from Nov 2 to Nov 3
₩159,529
₩189,663 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (2,474 reviews)
"It seems like this hotel saw its heyday in the early 2000s and they haven’t done anything to it since. It was giving “private equity”. The wallpaper in the bathroom was peeling, there was no hair dryer, no coffee maker. Our room didn’t even have shampoo. You have to pay extra for breakfast. That ..."

Reviewed on Oct 26, 2026

The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is ₩178,816 per night from Nov 22 to Nov 23
₩178,816
₩251,428 total
Nov 22 - Nov 23
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! (3,495 reviews)
"The first room that I was directed to the toilets were not clean and was full of waste. The bathtub was filled with water and the faucet was dripping. The carpet was not vacuumed and the bed looked like it was slept in. The second room I was directed to the carpet was not vacuumed and the sheets ..."

Reviewed on Oct 26, 2026

Hilton Chicago
See all 4,667 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 cityscape with tall skyscrapers and a historic tower.

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 large, historic building with a central tower and multiple windows, located near a body of water.

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