Glendale Vacation Packages 2026 from $467

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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!

The Latest Glendale Vacation Packages

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

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

$467

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$791

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$787

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Free upgrade was amazing and staff were even better. Thank you.

Reviewed on Oct 6, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$550

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

The check in staff were extremely rude

Reviewed on Oct 6, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$694

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

8.6/10 Excellent! (1,011 reviews)

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.

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.

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.

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.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Glendale Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$107 nightly

$127 total

Nov 2 - Nov 3

Total with taxes and fees

8/10 Very Good! (10,198 reviews)

"Old place, needs some love ( painting, repairs to walls, peeling wallpaper etc.) One working elevator of 2 ( to odd # rooms all in one area only?!) took forever. Had brkfst delivered one of our 2 mornings - tray was still there 24 hrs later. Stopped in cozy bar both nights and enjoyed the nice bartender! ..."

Reviewed on Oct 6, 2026

River Hotel

75 East Wacker Drive Chicago IL

$161 nightly

$191 total

Oct 25 - Oct 26

Total with taxes and fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (2,432 reviews)

"Great location and there is parking close by in a garage for $40 per night. The hotel itself is nice but the room we stayed in had stained carpets and couch cushions. Assuming all rooms are alike, rooms need a deep clean and some updates. Overall, pretty solid stay if you’re on a budget but want ..."

Reviewed on Oct 7, 2026

See all 4,739 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.