Half Day Vacation Packages

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    Save up to CA $1,096 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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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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,487, price is now CA $1,004 per person
CA $1,004
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
It’s a bit loud on the weekend. There is no daily housekeeping but great space and great location.

Reviewed on Apr 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,645, price is now CA $1,053 per person
CA $1,053
per person
Jun 11 - Jun 15
found 10 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Yessss it’s was amazing

Reviewed on Apr 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,916, price is now CA $1,246 per person
CA $1,246
per person
Jun 11 - Jun 15
found 10 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Hard to find the parking . Everything at navy pier closes at 8pm . Staff offered no extras even though it says we are vip Expedia and hiltons honors .

Reviewed on Apr 17, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,845, price is now CA $1,229 per person
CA $1,229
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,120 reviews)
The anti hero beer,the doorman,staff,the comfortable bed, shower 🚿,

Reviewed on Apr 18, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,268, price is now CA $1,580 per person
CA $1,580
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on Apr 7, 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

Downtown Chicago

5 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

Half Day Hotel Deals

Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
100 Barclay Blvd Lincolnshire IL
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from May 1 to May 2
CA $138
CA $155 total
May 1 - May 2
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
Coffee selection was great at breakfast. Breakfast area was kept neat, decent selection, and always replenished before it was all of the way empty. Beds were great, laundry machines filled quickly, took me two days to find an open one. I do wish there had been a way to wipe down the table in between ...

Reviewed on Apr 18, 2026

Staybridge Suites, Lincolnshire by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $341 per night from May 9 to May 10
CA $341
CA $400 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (2,266 reviews)
The room was spotless and the concierge service was excellent.

Reviewed on Apr 17, 2026

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

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $208 per night from Apr 26 to Apr 27
CA $208
CA $237 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (2,497 reviews)
Very convenient for travelers arriving late at O’Hare. The shuttle drivers are friendly and helpful, which makes a stressful travel day much easier. With flight delays becoming the “new normal” at ORD, staying near the airport on the first night is a practical solution. The hotel also offers excellent ...

Reviewed on Apr 18, 2026

Hyatt Regency O'Hare Chicago
See all 1,328 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Half Day vacation package cost?
Our Half Day packages, which start from as low as CA $1,004, 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.

Discover the most popular places to visit in Half Day

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.