Old Town Triangle Holidays
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Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
S$667
per person
21 Nov - 23 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Room was standard, close to millennium park, very helpful staff, & yummy restaurant!
Reviewed on 13 Oct, 2026
Sentral Michigan Avenue
Downtown Chicago
S$684
per person
21 Nov - 23 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,344 reviews)
We stayed here for 3 nights for the Chicago Marathon 2026, and while the location was fantastic, the overall hotel experience fell well short of expectations.
The Good:
Unbeatable Location: The biggest advantage of this hotel is its proximity to Grant Park. Being just a short walk from the marathon start and finish lines made race day logistics completely stress-free.
The Bad & Disappointing:
Closed Pool: We specifically selected and booked this hotel because of their great-looking pool. Unfortunately, the pool was closed for the entire 3-night duration of our stay. When we complained to the front desk, nobody offered any remedy, compensation, or gesture to make up for it, which was extremely disappointing.
Poor Kitchenware: The room included kitchen facilities, but the dishes provided were very limited, scratched, and visibly worn out/overused.
Other than that, the stay itself was just okay. However, given the lack of any support or remedy from staff regarding the closed pool, we likely wouldn't stay here again.
Reviewed on 14 Oct, 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.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Old Town Triangle
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$177
11 Nov - 12 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
S$232
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$218
2 Nov - 3 Nov
includes taxes & fees
8/10 Very good! (2,492 reviews)
"Let the buyer beware. The pics of the property are curated to make it appear as a Vintage but well maintained hotel. Vintage yes. Maintained no. The reception area is very appealing. But that is where the money is spent for upkeep.Once you leave that area everything is downhill. We arrived on our ..."
Reviewed on 14 Oct, 2026
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
How much does an Old Town Triangle holiday package cost?
The cheapest Old Town Triangle package is S$614, 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 travelling 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 holiday 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 travellers.
How far in advance should I book my Old Town Triangle holiday?
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 holiday 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 holiday 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 holiday 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.
Stay near popular Old Town Triangle attractions
Chicago History Museum
9.0/10 (37 reviews)
Explore the rich and exciting history of this great, iconic all-American city through an array of artefacts, hands-on exhibits and multi-media presentations.
Park West
8.8/10 (12 reviews)
You can enjoy a show at Park West on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
Second City
9.6/10 (15 reviews)
You can make plans for a show at Second City on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
Henry Gerber House
Learn about the local history of Chicago when you take a trip to Henry Gerber House. Stroll along the lakeside or visit the shops in this vibrant area.
Midwest Buddhist Temple
After visiting Midwest Buddhist Temple, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or visit the shops in this vibrant area.
Hudson Chess Park
Explore the great outdoors at Hudson Chess Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
Things to do
Skydeck Chicago at Willis Tower
S$54
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.