Deals on vacations and trips to Old Town Triangle

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Old Town Triangle flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
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
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Top Old Town Triangle hotel deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $167 per night
$167
per night
May 27 - May 28
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Breakfast available
Parking available
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $125 per night
$125
per night
May 29 - May 30
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking.
Pet friendly
Parking available
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
The price is $149 per night
$149
per night
May 27 - May 28
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pet friendly
Breakfast included
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $149 per night
$149
per night
May 27 - May 28
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $180 per night
$180
per night
May 29 - May 30
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Spa
Parking available
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $122 per night
$122
per night
May 27 - May 28
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Parking available
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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.

Popular places to visit

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 theater scene.

Second City

Photos of local treasures

Chicago History Museum showing interior views and signage

Frequently asked questions

How much are vacation packages to Old Town Triangle?
Exciting adventures await you in Old Town Triangle, with Travelocity vacation packages from as little as $398. Offering both hotels and flights, these awesome deals make it simple to explore every corner of the globe.
Where can I get the best vacation package deals for Old Town Triangle?
For a fun and affordable package deal to Old Town Triangle, you can’t go past Travelocity. Choose from 400 air carriers and 1,000,000 worldwide properties to create your dream escape — simple as that.
Why should I purchase my Old Town Triangle vacation bundle with Travelocity?
You’ll not only enjoy big savings, but you’ll also have access to our round-the-clock support, excellent service and a Price Match Guarantee. Roam across the world, discover hidden treasures and make lifelong memories — we’ll take care of the little details.
Will I save money on my Old Town Triangle car rental if I book it with my hotel or flight?
You certainly can — and booking one of our Old Town Triangle vacation packages is the easiest way to do this. Bundle any combination of a hotel, flight, car and experience and score great discounts. The more you bundle, the more you’ll save. There are loads of top attractions around Old Town Triangle to put on your itinerary, including Six Flags Great America (35 mi from Old Town Triangle). Nothing tops exploring places like this with the freedom of your own set of wheels.
What is the best time of year to go to Old Town Triangle?
March, April and June is high season here, while January, September and December are more quiet. If your budget is your first consideration, avoid traveling in as it tends to be the most expensive time. The cheapest month to explore this part of the world is .