Book the Best Old Town Chicago Hotels with Early Check-in in 2026 from CA $134 | Expedia.ca

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

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

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

Tonight

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Nov 10 - Nov 11

This weekend

Nov 13 - Nov 15

Next weekend

Nov 20 - Nov 22

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

A balcony with a table and chairs, a bottle of wine, and a glass of wine.

1. Kasa Magnificent Mile Chicago

River North, 2 km from Old Town Chicago

United States

Ricardo

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

2. Hotel Riu Plaza Chicago

Streeterville, 2.4 km from Old Town Chicago

Mexico

JESUS VERA

CA $262 total

includes taxes & fees

Nov 23 - Nov 24

A rooftop terrace with outdoor seating, a view of the city skyline, and a building with a brick facade.

3. The Chicago Hotel Collection Ambassador Gold Coast

1.1 km from Old Town Chicago

United States

Alicia

CA $195 total

includes taxes & fees

Nov 11 - Nov 12

A river with buildings on both sides, a bridge, and a pedestrian walkway.

4. River Hotel

The Loop, 2.9 km from Old Town Chicago

United States

Shelby

CA $178 total

includes taxes & fees

Dec 10 - Dec 11

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

5. Hilton Chicago/Magnificent Mile Suites

Streeterville, 2 km from Old Town Chicago

United States

Melissa

CA $170 total

includes taxes & fees

Dec 7 - Dec 8

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

6. Congress Plaza Hotel

The Loop, 4.2 km from Old Town Chicago

United States

Ashya

CA $195 total

includes taxes & fees

Nov 22 - Nov 23

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

7. L7 CHICAGO by LOTTE HOTELS

Theatre District, 3 km from Old Town Chicago

United States

Matthew

CA $219 total

includes taxes & fees

Nov 25 - Nov 26

A room with two chairs and a small table, a large window with a city view at night.

8. Eurostars Magnificent Mile

River North, 2.1 km from Old Town Chicago

United States

Gabriela

CA $242 total

includes taxes & fees

Nov 22 - Nov 23

A rooftop lounge with outdoor seating, a fire feature, and transparent dome structures.

9. The Chicago Hotel Collection - Magnificent Mile

Streeterville, 2.2 km from Old Town Chicago

United States

Silvia

CA $175 total

includes taxes & fees

Nov 23 - Nov 24

A cityscape with modern high-rise buildings, a river, and a boat.

10. Hyatt Regency Chicago

The Loop, 3 km from Old Town Chicago

United States

Kristee

CA $311 total

includes taxes & fees

Nov 22 - Nov 23

Lobby

11. The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 3 km from Old Town Chicago

United States

Kiera

CA $204 total

includes taxes & fees

Nov 22 - Nov 23

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

12. Embassy Suites by Hilton Chicago Downtown River North

River North, 2.3 km from Old Town Chicago

United States

Elyjah James

CA $184 total

includes taxes & fees

Nov 23 - Nov 24

A cityscape with tall buildings, a river, and a bridge.

13. The Royal Sonesta Chicago Downtown

The Loop, 2.9 km from Old Town Chicago

Canada

Frédéric

CA $270 total

includes taxes & fees

Nov 23 - Nov 24

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

14. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 2.9 km from Old Town Chicago

Switzerland

Kevin

CA $283 total

includes taxes & fees

Nov 23 - Nov 24

A warmly lit library with bookshelves, a central reading area with sofas and a table, and a chandelier.

15. Freehand Chicago

River North, 2.4 km from Old Town Chicago

United States

Rosemary

CA $207 total

includes taxes & fees

Dec 3 - Dec 4

The Intercontinental hotel facade with a large American flag and a floral display.

16. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 2.6 km from Old Town Chicago

Canada

Faye

CA $362 total

includes taxes & fees

Dec 10 - Dec 11

A modern building with a colorful facade and a red circular seating area.

17. citizenM Chicago Downtown

Theatre District, 3 km from Old Town Chicago

United States

Kristopher Joel

CA $195 total

includes taxes & fees

Nov 23 - Nov 24

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

18. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 2.6 km from Old Town Chicago

United States

Jodi

CA $163 total

includes taxes & fees

Dec 7 - Dec 8

A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.

19. Hilton Chicago

The Loop, 4.5 km from Old Town Chicago

United States

Jordan

CA $269 total

includes taxes & fees

Nov 26 - Nov 27

A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

20. Swissotel - Chicago

3.2 km from Old Town Chicago

United States

Oleg

CA $267 total

includes taxes & fees

Nov 26 - Nov 27

View all properties

Top Old Town Chicago Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent

"Incredible hotel n gorgeous lake view. Staff were so friendly and helpful. Loved it. Will stay here again for sure!"

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