Glendale Vacation Packages
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Your Glendale Vacation
Reserve a Glendale vacation package and prepare to experience all this city has to offer. Think about staying in the neighborhood of Magnificent Mile, which is good for cafes, shopping and history. Any trip to Glendale needs a well-thought-out itinerary. Fill yours with famous sights like Marquette Park, S.S. Peter and Paul Church and Balzekas Museum of Lithuanian Culture. Expedia has what you need to escape your routine. Tailor your vacation to Glendale to match your travel style, whatever that may be!
Top Holiday Package Deals in Glendale
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,088, price is now CA $735 per person
CA $735
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,054 reviews)
The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!
Reviewed on May 1, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,383, price is now CA $896 per person
CA $896
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,501, price is now CA $979 per person
CA $979
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,683, price is now CA $1,142 per person
CA $1,142
per person
Jul 9 - Jul 12
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again
Reviewed on May 6, 2026
Where to stay in Glendale
Find the best Glendale areas and neighborhoods for the activities you enjoy most. Learn more about Glendale
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.
Glendale Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 25 to May 26
CA $118
CA $182 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,689 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.
Reviewed on May 7, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from May 25 to May 26
CA $196
CA $233 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,177 reviews)
Oh, River Hotel, how do I hate you? Let me count the ways. It was very difficult to find the hotel. It's narrow and short squished between two buildings which are much bigger. The hotels directions are terrible. All I have to say is that it's right next to the Sofitel, and I would've found it immediately. ...
Reviewed on May 7, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from May 27 to May 28
CA $217
CA $297 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,081 reviews)
Centrally located hotel with breakfast included. Reasonable pricing for a new hotel. Recommended
Reviewed on May 7, 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
Discover the most popular places to visit in Glendale
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $61
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.