Hometown Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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Your Hometown Vacation

An easy way to experience this city is with a customized Hometown vacation package. Base yourself in the neighborhood of The Loop, which is great for bars and pubs, history and festivals or go someplace else — our package deals are all about you. Eager to venture out and explore? SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College are just a few of the most popular places to visit during your trip to Hometown. Browse Expedia's wide range of travel options and start organizing your ultimate vacation to Hometown today.

Top Hometown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 8 - Jul. 11
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 4
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (976 reviews)
Everything exceeded our expectations and would highly recommend! Stunning rooms that make the Ritz and Four Seasons look pathetic!

Reviewed on May 2, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (679 reviews)
There is such loud traffic nearby. I could not sleep for one minute.

Reviewed on May 13, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,005 reviews)
We have a plenty staying at this hotel has the best locations and restaurant is so good

Reviewed on May 13, 2024

Hometown Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is CA $220 per night from May 27 to May 28
CA $220
CA $259 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,732 reviews)
"A great and easy hotel to stay in for a short trip to Chicago! This location had everything you needed even an oven and microwave to use!"

Reviewed on May 13, 2024

Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is CA $143 per night from May 27 to May 28
CA $143
CA $189 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on May 14, 2024

Warwick Allerton - Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $257 per night from May 23 to May 24
CA $257
CA $335 total
includes taxes & fees
May 23 - May 24
8.6/10 Excellent! (1,000 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 4,119 properties in Hometown
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Hometown vacation package cost?
The cheapest Hometown vacation package is CA $1,085, so your dream getaway can become a reality — without a hefty price tag. Bundle flights, hotels, car rentals and more to build a package that suits you.
How do I get a cheap travel package to Hometown?
Our Hometown vacation packages mean plenty of savings for the savvy globetrotter. For the best deals, simply combine your flights, hotels and rental cars into a convenient package. But impressive bargains are just the beginning of your next memorable adventure. When you book with Expedia, and you’ll have over 550 airlines and 1,000,000 hotels across the globe to pick from. No matter your style, there’s a package here just for you.
Where should I stay in Hometown?
A vacation in Hometown wouldn’t be complete without stopping by Chicago Ridge Shopping Mall, Advocate Christ Hospital and Medical Center and Marquette Park. Spend your evenings near these popular sights and make sightseeing simple.
How far in advance should I book my Hometown vacation?
Reward yourself with the biggest variety and the lowest prices by booking your Hometown vacation nice and early. Airlines usually sell tickets around 12 months before departure, so start locking things in as soon as possible. Having said that, Expedia is constantly working to give you the best deals around, so it’s always a good time to book your dream vacation!
What does an Expedia Hometown travel package include?
With Expedia, you can select any combination of flights, hotels and car rentals to build your perfect Hometown travel package. Once you’ve made your booking, you can add on fun stuff like day tours and activities. Remember — the more you bundle, the bigger the savings!
What should I know before booking a Hometown travel package?
Whether it’s relaxation or adventure you’re chasing, a Hometown vacation package lets you organize your escape your way. Plus, you’ll get access to great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Hometown Expedia vacation package?
Yes, definitely. Expedia has more than 550 airline partners to choose from all over the world. With all that choice, finding the ideal carrier to take you to Hometown will be a cinch.
If I'm not able to travel, can I cancel my Hometown vacation package?
It’s impossible to predict what the future holds, so it’s good to know that you can change or cancel your Hometown vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for further details.

Discover the most popular places to visit in Hometown

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Hometown

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $311
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

CA $73
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Hometown

Other vacations you might like

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