Old Town Triangle Vacations

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Your Old Town Triangle Vacation

Whatever your travel style, you can see and do more with a customized Old Town Triangle vacation package. Spend your getaway enjoying this neighborhood's history and its other delights. Kick off your trip to Old Town Triangle by heading to nearby attractions such as Wrigley Field, Millennium Park and Willis Tower. Whatever your travel goals or the size of your budget, booking the ultimate Old Town Triangle vacation is simple with Expedia.

The Latest Old Town Triangle Vacation Packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
Well kept, great location and friendly staff!

Reviewed on May 31, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (664 reviews)
Nice property, excellent service. Hallways are showing a little wear. We have visited the Emily since its opening. Great neighborhood and nice hotel. Just a bit worn in the 3rd floor hallway.

Reviewed on Jun 2, 2024

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 25
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (1,731 reviews)
My room was modern and clean. The staff was friendly and helpful. It was generally quiet, although I was lucky enough to witness an Indian wedding on the street outside my window which was joyful and loud. A wonderful experience!

Reviewed on Jun 3, 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Beautiful property. Downtown convenient to everything

Reviewed on Jun 5, 2024

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

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.

Find hotel + flight trips 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
The price is $167 per night from Jun 16 to Jun 17
$167
$196 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,859 reviews)
"Friendly check in, gorgeous historic building. Room was great, bed and pillows comfortable, fresh. Charger ports on night stands. The water - lake view was absolutely worth the sunrise over Lake Michigan! Parked in. GRANT Parking South underground lot for about half the $62 parking next to the hotel, ..."

Reviewed on Jun 7, 2024

Congress Plaza Hotel
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
The price is $211 per night from Jul 7 to Jul 8
$211
$247 total
includes taxes & fees
Jul 7 - Jul 8
8/10 Very Good! (2,368 reviews)
"Had a great stay. Would definitely come back"

Reviewed on Jun 6, 2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $153 per night from Jul 7 to Jul 8
$153
$180 total
includes taxes & fees
Jul 7 - Jul 8
8.6/10 Excellent! (2,950 reviews)
"Excellent stay for us. The room was clean and comfortable. The staff was exceptional. Very professional and friendly. Couldn't ask for a better experience. Thanks."

Reviewed on Jun 5, 2024

River Hotel
See all 4,141 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Old Town Triangle vacation package cost?
The cheapest Old Town Triangle package is $395, so the trip of your dreams can become a reality — without a hefty price tag. Bundle flights, hotels, car rentals and more to tailor a package suited to your traveling style.
How do I get a cheap travel package to Old Town Triangle?
Combining your flight and hotel with Expedia won’t just save valuable time — it’ll save you a few dollars too. An Old Town Triangle vacation package makes it simple to create your dream adventure. With more than 550 airlines around the world to choose from, finding flights that fit your busy schedule won’t be a challenge. In addition to that, we’ve got over 1,000,000 properties globally to choose from. Now that’s what we call choice. No matter who you are, Expedia can show you the world.
Where should I stay in Old Town Triangle?
Take the leg work out of sightseeing by staying just a stone’s throw away from Old Town Triangle’s biggest attractions. Wrigley Field and Lincoln Park Zoo are two of the best in the area.
What are the top hotels in Old Town Triangle?
Whether you plan to stay for just one night or a week in Old Town Triangle, you’ll get a great night’s sleep at Hotel Lincoln, part of JdV by Hyatt. This place is a top pick for many travelers.
How far in advance should I book my Old Town Triangle vacation?
It’s hard to pick the best time for airfares, but we normally say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you’re booking late, don’t fret. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Old Town Triangle travel package include?
That depends on you. You can select from a range of Old Town Triangle packages, such as a rental car, hotel and flight. You can also book a hotel and a flight, or a rental car and a flight. Once you’ve made your booking, you can add the fun stuff like experiences and activities. Whatever your Old Town Triangle getaway looks like, get set to save!
What should I know before booking an Old Town Triangle travel package?
Our prices are always low. However, you’ll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia package, you’ll get transparent pricing and tons of choice.
Can I choose my airline with an Old Town Triangle Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Simply select your preferred air carrier and put together the perfect Old Town Triangle trip.
If I'm not able to travel, can I cancel my Old Town Triangle vacation package?
Because we know life can be unpredictable, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you’ve booked your Old Town Triangle vacation package in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Old Town Triangle

Image for Chicago History Museum

Chicago History Museum

4.5/5(23 reviews)

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

Chicago History Museum
Image for Park West

Park West

4.5/5(7 reviews)

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

Park West
Image for Second City

Second City

4.5/5(10 reviews)

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

Second City

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$188
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
94% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$89
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.