Half Day Vacation Packages
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Your Half Day Vacation
When you book a vacation package to Half Day, you can relax and enjoy your break knowing that all your travel plans are in order. Discover the wonders of this vibrant city while based in a neighborhood like Riverwoods, which is great for nature. If a sightseeing tour is part of the plan during your trip to Half Day, visit well-known attractions like Marriott Theatre, Edward L. Ryerson Conservation Area and Par-King Skill Golf. A few quick clicks is all it takes to craft a tailored Half Day vacation on Expedia.
Top Holiday Package Deals in Half Day
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,147, price is now CA $850 per person
CA $850
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
I’ve stayed at Talbott before and enjoyed it, but this time was pretty disappointing! Towel and amenity services were awful and the shower was very poor pressure.
Reviewed on Nov 8, 2026
Where to stay in Half Day
Find the best Half Day areas and neighborhoods for the activities you enjoy most. Learn more about Half Day
Downtown Chicago
4 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.
Half Day Hotel Deals
Courtyard by Marriott Chicago Lincolnshire
505 Milwaukee Ave Lincolnshire IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Nov 23 to Nov 24
CA $167
CA $187 total
Nov 23 - Nov 24
includes taxes & fees
Staybridge Suites, Lincolnshire by IHG
100 Barclay Blvd Lincolnshire IL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Nov 23 to Nov 24
CA $155
CA $174 total
Nov 23 - Nov 24
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $292 per night from Nov 29 to Nov 30
CA $292
CA $343 total
Nov 29 - Nov 30
includes taxes & fees
8.6/10 Excellent! (2,604 reviews)
"Nice rooms"
Reviewed on Nov 9, 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.
Frequently asked questions
Stay near popular Half Day attractions
Things to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.