Old Town Triangle Vacation Packages 2025 from $430

Old Town Triangle flight + hotel vacation packages

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

DoubleTree by Hilton Chicago Schaumburg

Save 100% on your flight

per person

Aug 6 - Aug 13

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, 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. Enjoy free perks like free self parking and an area shuttle.

Hilton Garden Inn Naperville/Warrenville

Save 100% on your flight

per person

Aug 6 - Aug 13

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a grocery/convenience store are also offered.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 17 - Jul 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 20 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and wedding services.

Hampton Inn Chicago/Naperville

Save 100% on your flight

per person

Aug 3 - Aug 8

found 18 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Top Old Town Triangle hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$150 total

Jul 1 - Jul 2

Total includes taxes and fees

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.

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$157 total

Jul 1 - Jul 2

Total includes taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Jun 29 - Jun 30

Total includes taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$198 total

Jun 30 - Jul 1

Total includes taxes and fees

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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Spa

Pet friendly

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$183 total

Jun 4 - Jun 5

Total includes taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.

Pet friendly

Free WiFi

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$231 nightly

$271 total

Jun 29 - Jun 30

Total includes taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

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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

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.

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.

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 fascinating museums.

Frequently asked questions

How much are vacation packages to Old Town Triangle?

With Travelocity vacation packages, you can be living it up in Old Town Triangle for as little as $430. Hotels, adventures and flights — we have it all. You’ll save a bunch just for bundling your bookings. And with all that taken care of before you even go, you won’t have to worry about a thing.

Where can I get the best vacation package deals for Old Town Triangle?

Landing the best package deal to Old Town Triangle is a breeze with Travelocity. With 400 air carriers and 1,000,000 worldwide properties, you won’t be short of choice when picking your hotels and flights.

Why should I purchase my Old Town Triangle vacation bundle with Travelocity?

Whether you’re searching for the ultimate unplugged escape or you crave the hustle and bustle that only a big city can provide, booking everything with Travelocity saves you time, money and hassle. No need to comb through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you’ll always score the lowest possible price, and our team of customer service experts are available 24/7 should you need them.

Will I save money on my Old Town Triangle car rental if I book it with my hotel or flight?

Most definitely — and booking one of our Old Town Triangle vacation packages is an excellent way to go about this. Bundle any combination of a car, hotel, flight and experience and score awesome discounts. The more you book, the more you’ll save. There are loads of landmarks in Old Town Triangle to stick on your itinerary, including Six Flags Great America (35 mi from Old Town Triangle). Nothing tops discovering thrilling places like this with the freedom of your own wheels.