Half Day Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $908
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (159 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,436
per person
Oct 2 - Oct 6
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Thanks for service

Reviewed on Sep 2, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,407
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,156
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $2,081
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (556 reviews)
Loved the hotel, super nice and clean! Felt like home away from home!

Reviewed on Sep 1, 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
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

Find hotels in The Loop
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Find hotels in Lincoln Park

Half Day Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $366
CA $429 total
Sep 27 - Sep 28
includes taxes & fees
8.4/10 Very good! (2,466 reviews)
"Mediocre quality for a Hilton. Rooms were dated not modern. Nothing special."

Reviewed on Sep 1, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
CA $249
CA $283 total
Sep 7 - Sep 8
includes taxes & fees
Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
CA $261
CA $306 total
Sep 26 - Sep 27
includes taxes & fees
8.6/10 Excellent! (1,379 reviews)
"Staff friendly shuttle service was great"

Reviewed on Sep 2, 2026

Marriott Chicago O'Hare
See all 1,252 properties in Half Day
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
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Romantic Vacations
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Frequently asked questions

How much does a Half Day vacation package cost?
Our Half Day packages, which start from as low as CA $908, are an easy way to save big bucks. Handpick your preferred hotels, flights and more to create a custom-built itinerary.
How do I get a cheap travel package to Half Day?
Combine your flight and hotel bookings, throw in extras such as tours, and save with a Half Day vacation package. You won't just walk away with exciting discounts on your adventure — you'll have a world of choice within your reach too. When you book with Expedia, you'll have your pick of over 550 airlines and 1,000,000 properties around the globe. Your next affordable adventure starts right here, right now!
Where should I stay in Half Day?
If you plan to visit Marriott Theatre, forget about commuting and find a place to stay close by. It's one of the most popular attractions in Half Day.
What are the top hotels in Half Day?
Lincolnshire Marriott Resort and Springhill Suites By Marriott Chicago Lincolnshire are two of the most well-known hotels in Half Day. Why not look up the amenities and rates at each and then decide?
How far in advance should I book my Half Day vacation?
Travelers are normally able to compare international airfares on Expedia up to 12 months prior to departure. Booking at the last minute? With a bit of luck, it's still possible to score an affordable ticket only weeks before your flight.
What does an Expedia Half Day travel package include?
Hotels, flights and a shiny set of wheels for all your fun road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on a few experiences and tours and watch your savings pile up. When it comes to organizing your Half Day escape, you're the boss!
What should I know before booking a Half Day travel package?
When you book your hotels, flights and car rentals together, you'll walk away with great discounts. Whether you're planning a beach escape in a villa or want to stay in a cozy apartment in the city, Expedia can help make it happen.
Can I choose my airline with a Half Day Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You get to decide. We have more than 550 airline partners around the world, so you have loads of choice when creating your Half Day escape.
If I'm not able to travel, can I cancel my Half Day vacation package?
Yes you can, and we'll help you every step of the way. You may be able to amend or cancel your Half Day vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your vacation, have a look at our Customer Service Portal for further information.

Stay near popular Half Day attractions

Marriott Theatre

9.0/10 (48 reviews)
You can make plans for a show at Marriott Theatre during your stay in Lincolnshire. Stroll along the lakeside or attend a sporting event in the area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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 Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.