Deals on vacations and trips to Old Town Triangle
Old Town Triangle flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $624, price is now $368 per person
$368
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $784, price is now $487 per person
$487
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $607, price is now $382 per person
$382
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Boston (BOS) 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, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $648, price is now $418 per person
$418
per person
Mar 20 - Mar 23
found 1 day 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 free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $570, price is now $374 per person
$374
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Top Old Town Triangle hotels deals
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $192 total per night
$192 total
Jan 20 - Jan 21
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $105 total per night
$105 total
Jan 25 - Jan 26
Total with 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.
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $193 total per night
$193 total
Jan 20 - Jan 21
Total with 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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $103 total per night
$103 total
Jan 30 - Jan 31
Total with taxes and fees
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. A snack bar/deli, express check-in, and express check-out are also on offer.
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $110 total per night
$110 total
Jan 20 - Jan 21
Total with taxes and fees
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand Chicago IL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $153 total per night
$153 total
Jan 20 - Jan 21
Total with taxes and fees
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
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See all available properties in Old Town Triangle
View all propertiesLowest 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
Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.
Park West
You can make plans for a show at Park West during your stay in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.
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 fascinating museums.
Frequently asked questions
Photos of local treasures
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