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.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $762
per person
Sep 24 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,518
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!

Reviewed on Aug 12, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $1,873
per person
Nov 5 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on Aug 10, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,379
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,412
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
I’m okay on them

Reviewed on Aug 11, 2026

Where to stay in Glendale

Find the best Glendale areas and neighborhoods for the activities you enjoy most. Learn more about Glendale
A busy city street with tall buildings, a bus, and cars.

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
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

Find hotels in The Loop
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Find hotels in Theatre District

Glendale Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $169
CA $201 total
Sep 7 - Sep 8
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $326
CA $382 total
Sep 12 - Sep 13
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,640 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
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Glendale vacation package cost?
Starting from as low as CA $762, 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.