Glendale Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,142, price is now CA $755 per person
CA $755
per person
Jul 1 - Jul 5
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,787, price is now CA $1,125 per person
CA $1,125
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on Apr 25, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,383, price is now CA $889 per person
CA $889
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (480 reviews)
The staff was friendly and the bed was very comfortable! Easy to find parking, many food options within walking distance.

Reviewed on Apr 21, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,447, price is now CA $941 per person
CA $941
per person
Jul 1 - Jul 5
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on Apr 27, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,140, price is now CA $1,398 per person
CA $1,398
per person
Jul 9 - Jul 12
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Wonderful Hotel will definitely be looking forward to going back.

Reviewed on Apr 25, 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

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.

Find hotels in Downtown Chicago

Glendale Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 26 to May 27
CA $118
CA $182 total
May 26 - May 27
includes taxes & fees
8.2/10 Very Good! (2,655 reviews)
It was ok

Reviewed on Apr 28, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $173 per night from May 25 to May 26
CA $173
CA $205 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,143 reviews)
Everything was great until morning then our room filled up with smoke otherwise it was good

Reviewed on Apr 27, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from May 25 to May 26
CA $134
CA $160 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,472 reviews)
Quite. Clean, Safe

Reviewed on Apr 27, 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,807 properties in Glendale
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Glendale vacation package cost?
Starting from as low as CA $755, you can create your own Glendale package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Glendale?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got it all. Pick and choose a combination that suits you and watch your savings pile up. Of course, a travel package is never a one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotel options globally, which lets you customize your Glendale getaway.
Where should I stay in Glendale?
With fascinating attractions like Marquette Park and S.S. Peter and Paul Church in this area, look for a hotel positioned near them. Balzekas Museum of Lithuanian Culture is another sight that people flock to.
How far in advance should I book my Glendale vacation?
Search Expedia to compare flights as soon as you know your travel dates. You can generally purchase a seat up to 12 months in advance. If you don't see your preferred air carrier, or you've left things to the last minute, fear not. The lowest prices to Glendale sometimes occur within weeks of departure.
What does an Expedia Glendale travel package include?
Travel packages include hotels, flights and rental cars, but you can combine any of them to create your dream Glendale trip. You can also add on a few tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll get discounts you won't find elsewhere.
What should I know before booking a Glendale travel package?
A package can be cheaper than separately booking all you need for your getaway. For example, combine your flights, hotels and rental cars and score big savings. Whatever sort of vacation you're planning, you're bound to find a package within your budget.
Can I choose my airline with a Glendale Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you definitely can. Just select your preferred carrier and put together the perfect Glendale vacation.
If I'm not able to travel, can I cancel my Glendale vacation package?
Yes, you can. We understand that life doesn't always go to plan, so we're here to help if you have to make changes to your Glendale vacation package. It may be possible to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Glendale

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.