A train passing through a tunnel with a curved roof and string lights.

Dearborn Homes 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

The Latest Dearborn Homes Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.
    Jan 21 - Jan 24

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $914
    CA $671
    per traveller
    found 15 hours ago
    Le Méridien Essex Chicago
  • A rooftop bar with seating and a view of the city skyline at night.
    Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,009 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    Save 100% on your flight
    CA $1,899
    CA $1,337
    per traveller
    found 15 hours ago
    The Peninsula Chicago
  • An outdoor seating area with a glass table, orange cushions, and potted plants.
    Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,885 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,107
    CA $794
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • A couple dining at a table with a view of a cityscape and a sunset.
    Jan 21 - Jan 24

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,801
    CA $1,316
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • A rooftop lounge with outdoor seating and a city skyline view.
    Jan 21 - Jan 24

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,344
    CA $984
    per traveller
    found 1 day ago
    Pendry Chicago

Where to stay in Dearborn Homes

Find the best Dearborn Homes areas and neighborhoods for the activities you enjoy most.
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

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 large, historic building with a central tower and multiple windows, located near a body of water.

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 river with a city skyline in the background, surrounded by green trees and grass.

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.

Dearborn Homes Hotel Deals

A multi-story building with a prominent entrance featuring a large archway and a sign.

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 3.5 km from Dearborn Homes
8.6 out of 10, Excellent, (3,536 reviews)
"Incredible hotel n gorgeous lake view. Staff were so friendly and helpful. Loved it. Will stay here again for sure!"
The price is CA $191
CA $269 total
includes taxes & fees
Nov 26 - Nov 27
Hilton Chicago
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.
See all properties in Dearborn Homes

Frequently Asked Questions

How much does a Dearborn Homes vacation package cost?

From as little as CA $671. Yes, you read that correctly. Our Dearborn Homes vacation packages are an easy way to stretch your budget further. Combine your favorite flights, hotels and rental car and get to know this popular destination.

How do I get a cheap travel package to Dearborn Homes?

Lock in flights that suit your schedule, add a hotel to your booking and watch how much you save with a Dearborn Homes vacation package. It's that easy! From hotels and flights to rental cars and activities, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1,000,000 properties worldwide to select from, you'll never be short of choice.

Where should I stay in Dearborn Homes?

Most people who visit Dearborn Homes include University of Chicago and Chicago Museum of Science and Industry on their bucket lists. Why not book a hotel as close as possible to these top attractions?

How far in advance should I book my Dearborn Homes vacation?

To bag rock-bottom prices, book as soon as you can. Air carriers generally release tickets, along with some of the lowest fares, up to a year prior to departure. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway in Dearborn Homes, there are always plenty of great deals on Expedia. Book your escape today!

What does an Expedia Dearborn Homes travel package include?

Hotels, flights and a cool set of wheels for all your road trip adventures. Simply choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on a couple of experiences and tours and watch your savings pile up. When it comes to organizing your Dearborn Homes escape, you're the one in control!

What should I know before booking a Dearborn Homes travel package?

Design deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we're a one-stop shop for all of them. You'll save precious dollars just for bundling your bookings. Whether you're going on a snow and ski adventure or kicking back on a warm beach, your ideal getaway is just a few clicks away.

Can I choose my airline with a Dearborn Homes Expedia vacation package?

Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our vacation packages give you the flexibility to pick from available flight, hotel or activity options that suit you.

If I'm not able to travel, can I cancel my Dearborn Homes vacation package?

Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Dearborn Homes vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, have a look at our Customer Service Portal for more information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.