Gage Park 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

Top Holiday Package Deals in Gage Park

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $872
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Close to every things, great location

Reviewed on Oct 16, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
CA $1,759
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

CA $1,565
per person
Dec 20 - Dec 27
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (3,460 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,198
per person
Nov 16 - Nov 19
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,029
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Everyone was so nice and accommodating. The location is great. We had a great view of the river.

Reviewed on Oct 15, 2026

Where to stay in Gage Park

Find the best Gage Park areas and neighborhoods for the activities you enjoy most. Learn more about Gage Park
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 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 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 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 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.

Find hotels in Lincoln Park

Gage Park Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $149
CA $177 total
Nov 11 - Nov 12
includes taxes & fees
Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $216
CA $257 total
Nov 1 - Nov 2
includes taxes & fees
River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
CA $183
CA $217 total
Nov 15 - Nov 16
includes taxes & fees
8/10 Very good! (2,400 reviews)
"Great central Chicago location; everything was walkable from this great hotel."

Reviewed on Oct 16, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,810 properties in Gage Park
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 Gage Park vacation package cost?
From as low as CA $872. Yes, you read that correctly. Our Gage Park packages are a simple way to make your budget go further. Combine your hotels, flights and rental car and get out and see this top destination.
How do I get a cheap travel package to Gage Park?
Combine your flights and hotels, add extras such as tours, and save with a Gage Park vacation package. You won't just walk away with wonderful discounts on your trip — you'll have loads of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 hotels around the world. Your next big adventure begins right here, right now!
Where should I stay in Gage Park?
With lots to explore in Gage Park, it'd be convenient for you to book a room in a hotel near its attractions. Marquette Park, St. Bernard Hospital and S.S. Peter and Paul Church are some top ones to put on your itinerary.
How far in advance should I book my Gage Park vacation?
It's hard to pick the best time for airfares, but we normally say the earlier, the better. Many international flights on Expedia become available to compare up to a year in advance. If you can't book ahead, don't fret. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Gage Park travel package include?
That depends on what you want. If you're traveling solo, you might decide to bundle hotels and flights. Taking the whole family to Gage Park? A travel package that includes flights, hotels and rental cars might suit you better. Expedia gives you the freedom and flexibility to customize your travel package.
What should I know before booking a Gage Park travel package?
When you book your hotels, flights and car rentals together, you'll land amazing discounts. Whether you're planning a mountain getaway in a cabin or would rather stay in a cozy apartment in the city, Expedia can help make it happen.
Can I choose my airline with a Gage Park Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you definitely can. Just select your favorite carrier and put together the perfect Gage Park trip.
If I'm not able to travel, can I cancel my Gage Park vacation package?
Yes, you can cancel your Gage Park booking if your plans have changed. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $59
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.