Old Town Triangle Vacations from $452
Book a Hotel + Flight or Car together to unlock savings
Your Old Town Triangle Vacation
Whatever your travel style, you can discover it all with a personalized Old Town Triangle vacation package. Spend your next escape uncovering this neighborhood'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 vacation into reality, no matter your travel plans or budget.
The Latest Old Town Triangle Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was $815, price is now $555 per person
$555
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)
Great location. Hotel just ok. Having a bar/restaurant below, was a convenience. However, you basically had to doordash to get them to deliver to your room... inconvenience. For the location, alone, I'd stay here again.
Reviewed on Nov 9, 2026
Pendry Chicago
Downtown Chicago
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
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
4 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.
Old Town Triangle Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 23 to Nov 24
$127 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (10,146 reviews)
"We stayed at the buckinham wing of the hotel. It’s an old hotel. The water runs brown for the first few seconds . The curtains were bright silver. Not what I expected. The best part is the location ."
Reviewed on Nov 9, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 10 to Nov 11
$138 total
Nov 10 - Nov 11
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Dec 10 to Dec 11
$126 total
Dec 10 - Dec 11
Total with taxes and fees
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.
Stay near popular Old Town Triangle attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.