Juda 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 Juda Vacation
Our vacation packages to Juda give you countless opportunities to enjoy new sights, sounds and activities. And with all the travel planning taken care of, you can breathe easy and enjoy your city getaway to the fullest. Eager to explore the sights but unsure where to begin? Every trip to Juda should include Sugar River Raceway. Check out Expedia's wide range of travel options and start organizing your perfect vacation to Juda today.
Top Juda Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,761, price is now CA $1,258 per person
CA $1,258
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Staff was amazing and the apartment building was phenomenally clean!
Reviewed on May 28, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,594, price is now CA $1,678 per person
CA $1,678
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.
Reviewed on May 28, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,878, price is now CA $1,339 per person
CA $1,339
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,017 reviews)
Everything was amazing! The women at the front desk, specifically Joy and Makaya, absolutely wonderful! Our day was perfect. Everything was considered and I have zero complaints. Absolutely will stay here again.!!
Reviewed on May 29, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,318, price is now CA $1,683 per person
CA $1,683
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
10/10 experience! Love this hotel!…the only negative was a less than nice /helpful staff person at the front desk of the spa when I asked about the use of the sauna/steam room and also my neighbors next to my room were quite loud
Reviewed on May 27, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $1,805, price is now CA $1,327 per person
CA $1,327
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,368 reviews)
Such a gorgeous hotel. And it’s in the Gold Coast neighbour of Chicago so you are in the middle of all the energy and excitement of the city. Absolutely amazing.
Reviewed on May 28, 2026
Juda Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $175 per night from Jun 25 to Jun 26
CA $175
CA $194 total
Jun 25 - Jun 26
includes taxes & fees
9/10 Wonderful! (896 reviews)
"Upon check-in, I informed the front desk staff that I was sorry in advance and that there was a baseball team coming to stay for the weekend. I was greeted with a less than warm response, saying they’re better not be any loud noise and she doesn’t want to deal with any complaints. The pool chlorine ..."
Reviewed on May 27, 2026
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Jun 25 to Jun 26
CA $125
CA $137 total
Jun 25 - Jun 26
includes taxes & fees
9/10 Wonderful! (859 reviews)
"Nice clean hotel on a main road very close to the Chalet Cheese Chop - great place! Ask for Tony and see if he will yodel for you! Delightful. There arecalso multiple restaurants from fast to sit down, a Dunkin (yay) and other things nearby. Good place to stay if in the area or going to New Glarus. ..."
Reviewed on May 27, 2026
Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Jun 21 to Jun 22
CA $151
CA $168 total
Jun 21 - Jun 22
includes taxes & fees
8.8/10 Excellent! (473 reviews)
"Room was clean, staff was nice, breakfast was fresh and tasty!"
Reviewed on May 4, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
