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

Boutique Hotels & Resorts in Old Town Chicago from AU$145

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Check availability on Old Town Chicago Boutique Hotels

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Our top choices for Old Town Chicago boutique hotels

1. Hotel Lincoln

Hotel Lincoln
4.0 star property
Old Town Chicago
8.0 out of 10, Very good, (1,162 reviews)
"Good stay and amenities."
United States
Charles
The price is AU$214
includes taxes & fees
19 Nov - 20 Nov
Hotel Lincoln

2. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 1.8 km from Old Town Chicago
8.4 out of 10, Very good, (3,970 reviews)
"Friendly staff and great location"
United States
Alexis
The price is AU$145
includes taxes & fees
23 Nov - 24 Nov
The Whitehall Hotel, BW Premier Collection

3. The Willows Hotel

The Willows Hotel
3.0 star property
2.5 km from Old Town Chicago
8.6 out of 10, Excellent, (1,005 reviews)
"Great staff and cute hotel. Everything was walking distance from hotel and highly recommend the hotel and neighborhood area."
United States
Cynthia
The price is AU$153
includes taxes & fees
30 Nov - 1 Dec
The Willows Hotel

4. The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
1.7 km from Old Town Chicago
9.4 out of 10, Exceptional, (194 reviews)
"Nice property overall Room was very nice Location excellent"
Canada
Michael
The price is AU$324
includes taxes & fees
23 Nov - 24 Nov
The Talbott, Autograph Collection

5. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 2.3 km from Old Town Chicago
9.0 out of 10, Wonderful, (1,955 reviews)
"Hotel is great for the price."
United States
alex
The price is AU$172
includes taxes & fees
23 Nov - 24 Nov
ACME Hotel Chicago, Outset Collection by Hilton

6. Hotel 505 River North

Hotel 505 River North
4.5 star property
River North, 2.4 km from Old Town Chicago
9.2 out of 10, Wonderful, (3,007 reviews)
"Great stay!"
United States
Miya
The price is AU$235
includes taxes & fees
22 Nov - 23 Nov
Hotel 505 River North

7. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 2.1 km from Old Town Chicago
9.0 out of 10, Wonderful, (3,985 reviews)
"Nice rooms and great location"
United States
Gabriela
The price is AU$245
includes taxes & fees
22 Nov - 23 Nov
Eurostars Magnificent Mile

8. Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
River North, 2 km from Old Town Chicago
8.4 out of 10, Very good, (3,167 reviews)
"Location was great. Front desk staff were friendly and helpful"
United States
Amy
The price is AU$218
includes taxes & fees
9 Nov - 10 Nov
Hotel Felix River North/Magnificent Mile

9. The Golden Arm

The Golden Arm
2.5 star property
2.8 km from Old Town Chicago
8.2 out of 10, Very good, (711 reviews)
"I had a great experience. The room was peaceful and clean. The location was perfect."
United States
Freda
The price is AU$233
includes taxes & fees
4 Nov - 5 Nov
The Golden Arm

10. The Majestic Hotel

The Majestic Hotel
3.0 star property
4 km from Old Town Chicago
9.0 out of 10, Wonderful, (1,037 reviews)
"It’s a charming hotel. Well located, and it was nice to have parking available."
United States
Sarah
The price is AU$195
includes taxes & fees
9 Nov - 10 Nov
The Majestic Hotel

11. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 2.2 km from Old Town Chicago
8.0 out of 10, Very good, (2,521 reviews)
"Great location, friendly staff, highly recommended."
United States
Silvia
The price is AU$177
includes taxes & fees
4 Nov - 5 Nov
The Chicago Hotel Collection - Magnificent Mile

12. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 3 km from Old Town Chicago
9.6 out of 10, Exceptional, (5,163 reviews)
"Amazing hotel will stay again"
United States
Matthew
The price is AU$245
includes taxes & fees
23 Nov - 24 Nov
L7 Chicago by LOTTE

13. Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 2.5 km from Old Town Chicago
8.8 out of 10, Excellent, (1,495 reviews)
"Really enjoyed my stay!"
United States
Raven
The price is AU$225
includes taxes & fees
24 Nov - 25 Nov
Ivy Boutique Hotel

14. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 4.1 km from Old Town Chicago
9.6 out of 10, Exceptional, (1,218 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is AU$272
includes taxes & fees
22 Nov - 23 Nov
Hilton Vacation Club Hotel Blake Chicago

15. Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 3 km from Old Town Chicago
9.0 out of 10, Wonderful, (1,548 reviews)
"Loved this stay as a solo traveler!"
United States
Macie
The price is AU$287
includes taxes & fees
22 Nov - 23 Nov
Sports Illustrated Resorts Chicago

16. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 3.6 km from Old Town Chicago
8.6 out of 10, Excellent, (2,337 reviews)
"The location is very convenient to go for restaurant, shopping and sightseeing."
Canada
Kenneth
The price is AU$181
includes taxes & fees
22 Nov - 23 Nov
Central Loop Hotel

17. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 3.3 km from Old Town Chicago
9.4 out of 10, Exceptional, (1,191 reviews)
"Great stay"
United States
RaeQuan
The price is AU$326
includes taxes & fees
22 Nov - 23 Nov
Staypineapple, An Iconic Hotel, The Loop

18. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
1.6 km from Old Town Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Great hotel"
United States
Luis
The price is AU$852
includes taxes & fees
22 Nov - 23 Nov
Waldorf Astoria Chicago

19. The Buckingham Hotel

The Buckingham Hotel
3.5 star property
The Loop, 4 km from Old Town Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
"It was a beautiful view had a good stay overall"
United States
Rachelle
The price is AU$256
includes taxes & fees
9 Nov - 10 Nov
The Buckingham Hotel

20. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
River North, 2.7 km from Old Town Chicago
9.6 out of 10, Exceptional, (2,076 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is AU$783
includes taxes & fees
15 Nov - 16 Nov
Trump International Hotel & Tower 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.

Find out more about Old Town Chicago

In the charming Old Town Chicago neighborhood, travellers can immerse themselves in a unique blend of history and modern flair. Start your day with a stroll along the picturesque streets, where you’ll find beautifully preserved Victorian architecture that tells the story of this vibrant community. Next, explore the area’s local artisan shops, showcasing everything from handmade crafts to one-of-a-kind artwork, perfect for finding a special memento. Food enthusiasts will delight in the variety of culinary experiences, including cozy eateries that serve up innovative dishes made from locally sourced ingredients. For a dose of culture, visit the nearby art galleries and boutique studios that feature the works of local artists, offering an intimate glimpse into the creative spirit of the neighborhood. Lastly, embrace the lively atmosphere by enjoying a leisurely evening at one of the charming cocktail lounges, where you can unwind with expertly crafted drinks while soaking in the local vibe. After a day filled with exploration, retreat to a boutique hotel that embodies the essence of Old Town, where personalized service and thoughtful amenities ensure a memorable stay.

Top Old Town Chicago Hotel Reviews

Frequently asked questions

What's the best boutique accommodation in Old Town Chicago?
Hotel Lincoln is a favourite hotel with Expedia travellers looking for a stylish stay, and features a rooftop terrace and a 24-hour fitness centre.
What's there to see and do in Old Town Chicago?
Visitors speak positively about this destination's fantastic nightlife, major shopping centres and panoramic lake views. While you're out and about in Old Town Chicago, popular attractions like Navy Pier, Wrigley Field and Soldier Field are worth a visit. You might also want to see spots like Michigan Avenue, Second City and Armitage Avenue during your trip.
What's the best way to get to my boutique hotel in Old Town Chicago?
You have a few options for travelling to and around Old Town Chicago. The nearest major airport is Chicago Midway Airport (MDW), which is located 10 mi (16 km) away, but Chicago O'Hare International Airport (ORD) may also be an option. Metro stations nearby include Sedgwick Station and Clark-Division Station.

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