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
Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 7 - Aug 10

    JW Marriott Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    "Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities "
    Reviewed May 3, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $1,294
    CA $946
    per traveller
    found 21 hours ago
    JW Marriott Chicago
  • Terrace/patio
    Jun 26 - Jun 29

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,502 reviews)
    "The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay."
    Reviewed May 20, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,890
    CA $1,297
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Lounge
    Jul 23 - Jul 26

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,126 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,763
    CA $1,251
    per traveller
    found 1 day ago
    Pendry Chicago
  • Exterior
    Jul 13 - Jul 17

    Hilton Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,802 reviews)
    "Since we have checked in, I have gotten 3 charges! Fees they don't tell you when you check in. I have been charged even after check out and no one is responding."
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,558
    CA $1,118
    per traveller
    found 1 day ago
    Hilton Chicago
  • Terrace/patio
    Jun 26 - Jun 29

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,875 reviews)
    "Great experience! Would stay here agin"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,102
    CA $1,527
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

Where to stay in Dearborn Homes

Find the best Dearborn Homes areas and neighborhoods for the activities you enjoy most. Learn more about Dearborn Homes
Downtown Chicago

Downtown Chicago

5 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

Dearborn Homes Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,122 reviews)
"Good for a sleep and go. Not horrible, certainly not the best hotel i've ever stayed at."

Reviewed on May 20, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 25 to May 26
CA $205
CA $283 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,202 reviews)
"Good"

Reviewed on May 21, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,449 reviews)
"Great stay"

Reviewed on May 21, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,637 properties in Dearborn Homes
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 Dearborn Homes vacation package cost?
From as little as . 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.

Discover the most popular places to visit in Dearborn Homes

Wrigley Field

Wrigley Field

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

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

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
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
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.