Hometown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,304
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
The Stable hotel was extremely nice and well taken care of, the staff was very nice and helpful also, i would definitely stay again! Also the views from the room were amazing!
Reviewed on Sep 13, 2026
Ready to book your vacation to Hometown?
Hometown Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
CA $213
CA $254 total
Sep 27 - Sep 28
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $248
CA $295 total
Oct 13 - Oct 14
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $220
CA $262 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very good! (10,237 reviews)
"Very noisy. If you're lucky to get a connected room, that has a door instead of a wall between the rooms, with a very loud guest, when they watch TV at 11PM or when they wake up a 6 AM, then you can forget about getting any sleep 😀"
Reviewed on Sep 13, 2026
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.
What to do in Hometown
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Frequently asked questions
How much does a Hometown vacation package cost?
You'll find cheap prices from CA $925 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?
- 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.
- 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.
- 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.
- 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
