Hometown Vacation Packages

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    Save up to CA $1,096 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Nov 6 - Nov 9
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,008 reviews)
Great location and beautiful hotel with nice rooms and awesome rooftop!

Reviewed on Aug. 10, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Terrace 16 resto has the best view in Chicago outstanding service. Hotel is located right next to the river cruises. Walgreens is 3 minutes away by foot. Very safe neighborhood several excellent restaurants within 10 minutes on foot. Try Wildberry resta for breakfast excellent food. Sanda for Asian food and Grand Boucher French The pizza place next to hotel (bonjiourno) overrated and subpar

Reviewed on Aug. 12, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location was good. Staff was friendly. It was clean. But it was hard to enjoy time in the room because of the TV. They had horrible cable with nothing on, and it wasn’t a smart tv so we couldn’t log into any of our streaming services or even stream from our phones to the tv. We had to go out and buy a firestick.

Reviewed on Aug. 10, 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
Nov 6 - Nov 9
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,829 reviews)
Helpful staff, beautiful hotel in a great location!

Reviewed on Aug. 12, 2025

Ready to book your vacation to Hometown?

 

Choose your dates

Hometown 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 $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,958 reviews)
"Super convenient to everything we needed or wanted Hotel is good, location is great"

Reviewed on Aug. 11, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Sep 4 to Sep 5
CA $239
CA $315 total
Sep 4 - Sep 5
includes taxes & fees
8.4/10 Very Good! (1,848 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on Aug. 11, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 3 to Sep 4
CA $186
CA $219 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (3,648 reviews)
"Good"

Reviewed on Aug. 10, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,525 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Hometown

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Hometown

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Hometown

Frequently asked questions

How much does a Hometown vacation package cost?
You'll find cheap prices from CA $541 on Expedia for your Hometown getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Hometown costs.
What are the cheapest months to go to Hometown?
You can generally find lower prices and better availability in January, February and November. Browse our cheap Hometown vacation packages and you could score some great off-season discounts.
How many days is enough for Hometown?
Hometown vacations can be as short or long as you like, but to really sink your teeth into this destination, we'd suggest 2 days is a good ballpark. With this timeframe, you can visit major attractions like Moraine Valley Community College Fine and Performing Arts Centre and Lake Katherine Nature Centre along with underrated gems. Don't forget to visit cool neighbourhoods such as Archer Heights and Clearing either. If you're clever with your time, you can even schedule a day trip from Hometown too.
How to find the best Hometown package deals?
Finding a cheap Hometown package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Hometown package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Hometown vacation as a package?
You can enjoy significant savings on your Hometown retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Hometown?
If you have your Hometown travel dates confirmed, book early to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Hometown?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Hometown.
  2. Set your budget: Consider costs such as flights, meals and transportation when calculating how much to set aside for your trip to Hometown. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Decide how many days away: Start by making a list of all the attractions you want to experience in Hometown. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Hometown vacation package.

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