Explore top 2026 4 Star Hotels in Old Town Triangle

Name: Pendry Chicago
Price range: $350 total
Rating: 9.2

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Top Old Town Triangle 4 Star hotels

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$246 nightly

$288 total

Sep 5 - Sep 6

Total with taxes and fees

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

Fully refundableReserve now, pay when you stay

$211 nightly

$251 total

Sep 1 - Sep 2

Total with taxes and fees

This hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, ...

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Aug 30 - Aug 31

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, ...

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

$169 nightly

$193 total

Aug 30 - Aug 31

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...

9/10 Wonderful! (3,001 reviews)

"Staff members were helpful and friendly. Cleaned room."

Reviewed on Aug 15, 2026

Fairmont Chicago at Millennium Park

200 North Columbus Drive Chicago IL

Fully refundableReserve now, pay when you stay

$295 nightly

$351 total

Sep 8 - Sep 9

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room ...

8.8/10 Excellent! (2,296 reviews)

"The staff at the property was very accommodating."

Reviewed on Aug 14, 2026

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St Chicago IL

Fully refundableReserve now, pay when you stay

$222 nightly

$264 total

Aug 30 - Aug 31

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. ...

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL

Fully refundableReserve now, pay when you stay

$250 nightly

$297 total

Sep 7 - Sep 8

Total with taxes and fees

This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, ...

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$194 nightly

$230 total

Sep 7 - Sep 8

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...

8.6/10 Excellent! (3,039 reviews)

"Great location, amazing staff"

Reviewed on Aug 15, 2026

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave Chicago IL

$283 nightly

$337 total

Aug 23 - Aug 24

Total with taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the sauna and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee ...

9.2/10 Wonderful! (3,182 reviews)

"A grand old dame of a hotel, with emphasis on the grand. Although I would skip the in-house restaurants entirely, the place is well-maintained, well-run, with strong service and with a marvelous pool the likes of which one rarely sees. The location is two blocks from the Chicago river. The building ..."

Reviewed on Aug 15, 2026

Pendry Chicago

230 North Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$295 nightly

$350 total

Aug 31 - Sep 1

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a ...

9.2/10 Wonderful! (1,155 reviews)

"Everyone at the Pendry was super nice. I would definitely recommend this hotel. My friend got sick and they offered to run across the street to get her medicine. Exceptional service."

Reviewed on Aug 12, 2026

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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.