A street with outdoor seating, brick buildings, and signs for a barbershop and a restaurant.

Find Hotels with Early Check-in in Old Town Chicago, IL

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Check availability on Old Town Chicago Hotels with Early Check-in

Our top choices for Old Town Chicago hotels with express check-in

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Streeterville, 1.8 km from Old Town Chicago
9.4 out of 10, Exceptional, (1,003 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is NT$16,755
NT$19,919 total
includes taxes & fees
Nov 22 - Nov 23
Four Seasons Hotel Chicago

2. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
River North, 2.3 km from Old Town Chicago
8.6 out of 10, Excellent, (5,990 reviews)
"Amazing stay!"
United States
Elyjah James
The price is NT$3,142
NT$4,282 total
includes taxes & fees
Nov 23 - Nov 24
Embassy Suites by Hilton Chicago Downtown River North

3. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Streeterville, 2.1 km from Old Town Chicago
9.8 out of 10, Exceptional, (1,009 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is NT$19,711
NT$23,435 total
includes taxes & fees
Dec 6 - Dec 7
The Peninsula Chicago

4. Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North
3.0 star property
River North, 1.9 km from Old Town Chicago
8.4 out of 10, Very good, (2,252 reviews)
"Breakfast was great and location was great for the shopping we were doing."
United States
Bette
The price is NT$3,602
NT$4,283 total
includes taxes & fees
Nov 22 - Nov 23
Home2 Suites by Hilton Chicago River North

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
1.6 km from Old Town Chicago
9.4 out of 10, Exceptional, (1,004 reviews)
"Very clean and upscale property. Lovely amenities. Great location and staff very friendly."
United States
Loai
The price is NT$14,660
NT$17,430 total
includes taxes & fees
Dec 6 - Dec 7
Waldorf Astoria Chicago

6. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 2.5 km from Old Town Chicago
9.0 out of 10, Wonderful, (1,004 reviews)
"Very clean property. Very friendly staff and perfect location."
United States
Nancy
The price is NT$3,402
NT$4,044 total
includes taxes & fees
Dec 6 - Dec 7
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

7. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 2.5 km from Old Town Chicago
8.6 out of 10, Excellent, (3,315 reviews)
"Great location . Would definitely come back there"
United States
Kevin
The price is NT$3,713
NT$4,415 total
includes taxes & fees
Nov 22 - Nov 23
Aloft by Marriott Chicago Mag Mile

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Streeterville, 2.1 km from Old Town Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is NT$15,153
NT$18,015 total
includes taxes & fees
Dec 8 - Dec 9
The Ritz-Carlton, Chicago

9. Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 1.9 km from Old Town Chicago
8.6 out of 10, Excellent, (1,942 reviews)
"Very good location, great staff, clean rooms"
United States
ray
The price is NT$3,548
NT$4,999 total
includes taxes & fees
Nov 22 - Nov 23
Millennium Hotel Knickerbocker Chicago

10. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
3.2 km from Old Town Chicago
9.0 out of 10, Wonderful, (3,583 reviews)
"Good location and nice hotel"
United States
Oleg
The price is NT$4,254
NT$6,215 total
includes taxes & fees
Nov 26 - Nov 27
Swissotel - Chicago

11. The Drake

The Drake
4.0 star property
Streeterville, 1.8 km from Old Town Chicago
9.0 out of 10, Wonderful, (1,663 reviews)
"Fantastic hotel! Staff, service, atmosphere were all top notch!"
United States
stephanie
The price is NT$4,553
NT$5,413 total
includes taxes & fees
Nov 22 - Nov 23
The Drake

12. River Hotel

River Hotel
4.0 star property
The Loop, 2.9 km from Old Town Chicago
8.8 out of 10, Excellent, (5,605 reviews)
"The hotel was in a great location."
United States
Shelby
The price is NT$3,482
NT$4,140 total
includes taxes & fees
Dec 10 - Dec 11
River Hotel

13. Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 2.4 km from Old Town Chicago
9.0 out of 10, Wonderful, (1,118 reviews)
"Amazing location & great staff."
United States
Angela
The price is NT$3,602
NT$5,259 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Centric Chicago Magnificent Mile

14. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 3 km from Old Town Chicago
9.4 out of 10, Exceptional, (3,506 reviews)
"Wonderful will stay again"
United States
Kristee
The price is NT$5,099
NT$7,234 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt Regency Chicago

15. L7 CHICAGO by LOTTE HOTELS

L7 CHICAGO by LOTTE HOTELS
4.5 star property
Theatre District, 3 km from Old Town Chicago
9.6 out of 10, Exceptional, (5,206 reviews)
"Amazing hotel will stay again"
United States
Matthew
The price is NT$4,763
NT$5,663 total
includes taxes & fees
Nov 24 - Nov 25
L7 CHICAGO by LOTTE HOTELS

16. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 3.2 km from Old Town Chicago
8.8 out of 10, Excellent, (2,341 reviews)
"Loved my stay"
Canada
Joel
The price is NT$6,538
NT$8,945 total
includes taxes & fees
Nov 24 - Nov 25
Fairmont Chicago at Millennium Park

17. Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile
4.0 star property
Streeterville, 2.5 km from Old Town Chicago
9.0 out of 10, Wonderful, (1,023 reviews)
"Great stay"
United States
DaVod
The price is NT$6,045
NT$8,358 total
includes taxes & fees
Nov 23 - Nov 24
Chicago Marriott Downtown Magnificent Mile

18. Kinzie Hotel

Kinzie Hotel
4.0 star property
River North, 2.6 km from Old Town Chicago
9.2 out of 10, Wonderful, (2,182 reviews)
"I would stay here again in the future. Perfect location."
United States
Ken
The price is NT$5,292
NT$7,204 total
includes taxes & fees
Dec 6 - Dec 7
Kinzie Hotel

19. Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 2.3 km from Old Town Chicago
9.6 out of 10, Exceptional, (670 reviews)
"The entire stay was excellent, will definitely visit again."
United States
JERI
The price is NT$4,172
NT$4,960 total
includes taxes & fees
Nov 22 - Nov 23
Residence Inn Chicago Downtown Magnificent Mile

20. The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
4.0 star property
River North, 2.3 km from Old Town Chicago
8.8 out of 10, Excellent, (1,558 reviews)
"Great hotel - fabulous location!! We enjoyed our stay."
United States
Nolan
The price is NT$4,238
NT$6,016 total
includes taxes & fees
Nov 25 - Nov 26
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
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.

Find out more about Old Town Chicago

Discover top Old Town Chicago attractions

Old Town Chicago is a vibrant neighborhood packed with charm and history, perfect for travelers seeking quality experiences. Begin your exploration at the iconic Second City, where you can enjoy a night of laughs with some of the best improv comedy in the country. Just a short walk away, the picturesque Old Town Triangle Historic District invites you to stroll through its quaint streets lined with Victorian-era homes, providing a glimpse into the city's architectural past. For a taste of local culture, visit the Old Town Art Fair, held annually and featuring works from local artists, or explore the lively farmers market for fresh produce and artisanal goods. Don't miss a visit to the nearby Lincoln Park Zoo, where families can enjoy free admission to see wildlife in a beautifully landscaped setting. When it comes to accommodations, staying in one of the boutique hotels in Old Town allows you to enjoy personalized service and a touch of luxury. Many offer spacious rooms with modern amenities, and some even feature rooftop terraces with stunning views of the city skyline, providing a relaxing retreat after a day of adventure. With its unique blend of historic charm and contemporary conveniences, Old Town Chicago is sure to make your stay memorable.

Top Old Town Chicago Hotel Reviews

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