
Old Town Triangle Holidays from AU$2,911
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your Old Town Triangle Holiday
Whatever your travel style, you can discover it all with a personalised Old Town Triangle holiday package. Spend your next escape uncovering this neighbourhood's history and its other charms. Some top nearby attractions to visit during your trip to Old Town Triangle include Wrigley Field, Millennium Park and Willis Tower. Expedia can help turn your ideal Old Town Triangle holiday into reality, no matter your travel plans or budget.
Top Holiday Package Deals in Old Town Triangle
Price found within the past 48 hours. Click for updated prices.

Radisson Blu Aqua Hotel Chicago
Downtown Chicago
per person
17 Oct - 24 Oct
found 10 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,586 reviews)
We had corner king room and it was very nice! We saw the city and the pool. The only thing I didn’t like was no complimentary water and cookies like most hotels. Sometimes the water be on point after walking and traveling. It’s thoughtful.
Reviewed on 12 Aug. 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
17 Oct - 24 Oct
found 10 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Terrace 16 resto has the best view in Chicago outstanding service.
Hotel is located right next to the river cruises.
Walgreens is 3 minutes away by foot.
Very safe neighborhood several excellent restaurants within 10 minutes on foot.
Try Wildberry resta for breakfast excellent food.
Sanda for Asian food and Grand Boucher French
The pizza place next to hotel (bonjiourno) overrated and subpar
Reviewed on 12 Aug. 2025


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
17 Oct - 24 Oct
found 10 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Everything was beautiful close to dining and shopping the beds were comfortable it was so relaxing looking out the window unto the ocean. Don’t hesitate book now
Reviewed on 11 Aug. 2025
Our guide on where to stay in Old Town Triangle
Find the best Old Town Triangle areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Triangle

Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Our pick of the best Old Town Triangle Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$242 per night from 1 Sept to 2 Sept
AU$242
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,945 reviews)
"I love the location."
Reviewed on 11 Aug. 2025

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$351 per night from 21 Aug to 22 Aug
AU$351
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (1,848 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."
Reviewed on 11 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$244 per night from 2 Sept to 3 Sept
AU$244
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (3,660 reviews)
"Great rooms, comfortable, walking distance to anywhere you’d want to go."
Reviewed on 10 Aug. 2025
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.
Frequently asked questions
Activities

Chicago By Night River & Lake Cruise
AU$69
per adult
96% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
AU$62
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.