Half Day Vacations from ￥307,881

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    Save up to ￥45,448 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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The Latest Half Day Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥389,445, price is now ￥307,881 per person
￥307,881
per person
May 20 - May 25
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,136 reviews)
Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries.

Reviewed on Mar 1, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥629,236, price is now ￥449,760 per person
￥449,760
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
This hotel was super nice and it was clean and we did have to use another hotels valet, but it was no problem because it was right next-door, but the staff was super nice and accommodating. I will definitely stay here again.

Reviewed on Mar 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥684,328, price is now ￥533,808 per person
￥533,808
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.

Reviewed on Mar 3, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥543,210, price is now ￥434,640 per person
￥434,640
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥511,058, price is now ￥414,530 per person
￥414,530
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,700 reviews)
My stay at The Wade overall was pretty good. I booked here because it has a pool, and I thought I would have a nice view (city view). The view wasn’t available, I was on the 27th floor and only had a view of the roof of other buildings, and other apartments. I kept the window covered for the most part. The pool was unkept in my opinion, I didn’t feel comfortable with the dirt ring on the white tile that surrounded the pool, and the water looked and felt pretty grimy, I felt it needed to be serviced. Though my main attractions to this location were not fulfilled it was very quiet on my floor, the cleaning crew were very polite and generous, and the valet was very friendly and always gave me great service despite it being very busy over the course of my stay.

Reviewed on Mar 2, 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 showing a city

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

Half Day Hotel Deals

Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
1501 Sherman Ave Evanston IL
Fully refundable
8.6/10 Excellent! (1,806 reviews)
Clean and great helpful staff

Reviewed on Mar 2, 2026

Get rates
Holiday Inn Chicago North-Evanston 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 ￥30,761 per night from Mar 27 to Mar 28
￥30,761
￥36,110 total
Mar 27 - Mar 28
includes taxes & fees
8.4/10 Very Good! (2,224 reviews)
Yed

Reviewed on Mar 4, 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
Fully refundableReserve now, pay when you stay
The price is ￥19,879 per night from Mar 8 to Mar 9
￥19,879
￥22,658 total
Mar 8 - Mar 9
includes taxes & fees
8.8/10 Excellent! (2,385 reviews)
Convenient, great amenities, good food

Reviewed on Mar 5, 2026

Hyatt Regency O'Hare Chicago
See all 1,348 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.

Frequently asked questions

How much does a Half Day vacation package cost?
Our Half Day packages, which start from as low as ￥307,881, 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 featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,860
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

￥5,928
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.