Old Town Triangle Vacations from $255

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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.
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $437, price is now $255 per person
$255
per person
Nov 14 - Nov 16
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (146 reviews)
Popular with drunks that party way past reasonable quiet hours.

Reviewed on Sep 27, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $638 per person
$638
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,098, price is now $543 per person
$543
per person
Nov 10 - Nov 16
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
First time in Chicago, the hotel was walkable to a lot of things. Loved the location. Was clean and felt comfortable.

Reviewed on Oct 5, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,180, price is now $613 per person
$613
per person
Nov 10 - Nov 16
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
This hotel was very nice however they have one elevator that was working for 36 floors. We constantly had to wait for the elevator and sometimes we waited so long that we decided to take the stairs and walk down 14 flights, we ended up doing this 3 times. This was incredibly inconvenient! When the elevator was working, it stopped on every single floor as we went down. We were there from Wednesday to Sunday, it was very frustrating!

Reviewed on Oct 5, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,206, price is now $654 per person
$654
per person
Nov 10 - Nov 16
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Front desk clerk was great. Made us feel like VIPs.

Reviewed on Oct 5, 2025

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 showing a city

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.

Find hotels in Downtown Chicago

Old Town Triangle Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,314 reviews)
"Spotless room. Shops nearby"

Reviewed on Oct 5, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $113 total per night from Nov 4 to Nov 5
$113 total
Nov 4 - Nov 5
Total with taxes and fees
7.8/10 Good! (2,419 reviews)
Great stay
"This weekend was a full house but even with there being so many people for the dorm rooms the staff still tried to accommodate as much as possible."

Reviewed on Oct 5, 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $196 total per night from Nov 4 to Nov 5
$196 total
Nov 4 - Nov 5
Total with taxes and fees
8.4/10 Very Good! (5,042 reviews)
"Will stay again"

Reviewed on Oct 5, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,501 properties in Old Town Triangle
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Old Town Triangle

Chicago History Museum featuring interior views

Chicago History Museum

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

Chicago History Museum
Three of the Five Horses adorning Park West Park

Park West

You can make plans for a show at Park West during your stay in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Park West

Second City

You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Second City

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.