Half Day Holidays from £719

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Packages with flights are ATOL protected

Your Half Day Holiday

When you book a holiday 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 neighbourhood 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 holiday on Expedia.

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £898, price is now £719 per person
£719
per person
20 Jan - 24 Jan
found 16 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Not worth it for the money. Good location but nothing special.

Reviewed on 8 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,797, price is now £1,324 per person
£1,324
per person
25 Dec - 30 Dec
found 15 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Very good service

Reviewed on 9 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 16 hours ago
Return direct flight included
London (LON) 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 8 Nov 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,079, price is now £841 per person
£841
per person
11 Jan - 16 Jan
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,202, price is now £955 per person
£955
per person
20 Jan - 24 Jan
found 16 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,309 reviews)

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

Top hotels in Half Day

Courtyard by Marriott Chicago Lincolnshire

Courtyard by Marriott Chicago Lincolnshire

3 out of 5
505 Milwaukee Ave Lincolnshire IL
Fully refundableReserve now, pay when you stay
The price is £99 per night from 23 Nov to 24 Nov
£99
23 Nov - 24 Nov
includes taxes & fees
Courtyard by Marriott Chicago Lincolnshire
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 £92 per night from 23 Nov to 24 Nov
£92
23 Nov - 24 Nov
includes taxes & fees
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 £182 per night from 29 Nov to 30 Nov
£182
29 Nov - 30 Nov
includes taxes & fees
8.6/10 Excellent! (2,604 reviews)
"Nice rooms"

Reviewed on 9 Nov 2026

Hilton Chicago O'Hare Airport
See all 1,274 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Half Day travel package cost?
Discover the best of Half Day from as low as £719. Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few activities or tours to your package.
If I'm not able to travel, can I cancel my Half Day travel package?
Whether it's your hotel, flight or rental car, you can cancel or change it. Locked in your Half Day travel package in the last 24 hours? You may be able to make changes at no cost. For bookings older than that, you may be charged a fee by your airline, hotel or car rental company. For more details, visit our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Half Day?
Bundle your hotels and flights with Expedia to save big on your next exciting adventure. With over 550 airlines and 1,000,000 hotel options across the world, your Half Day holiday package can be tailored exactly to suit your travel style. With all that extra cash, why not include one or two interesting tours and activities? It's an easy way to unlock even more discounts. Your dream holiday in Half Day is much closer than you thought!
Does Expedia offer Book Now, Pay Later Half Day holidays?
Expedia has partnered with online lender Klarna to make your next break easier on your hip pocket. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find one that suits your budget. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can take that well-deserved holiday now.
  • Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan with Klarna.

Where should I stay in Half Day?
If you plan to check out Marriott Theatre, maximize your time sightseeing and stay close by. It's one of the top attractions in the area.
What are the top hotels in Half Day?
If it's your first time staying in Half Day, lock in a room at Lincolnshire Marriott Resort or Staybridge Suites, Lincolnshire, an IHG Hotel. Both hotels offer comfy beds and are popular options with many travellers.
How far in advance should I book my Half Day holiday?
Get rewarded with the widest variety at the cheapest prices by booking your adventure to Half Day early. Airlines tend to release tickets around a year prior to departure, so secure your spot ASAP. That said, Expedia is dedicated to giving you the best bargains around, so it's never a bad time to book your dream holiday!
What does an Expedia Half Day travel package include?
It comes down to what kind of getaway you're thinking about. Half Day travel deals can include hotels, flights and car rentals. You can mix and match to find the bundle that suits your budget and style. You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking a Half Day travel package?
When you book your hotels, flights and car rentals together, you'll pick up great discounts. Whether you're planning a rural escape in a cottage or want to stay in a comfortable hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Half Day Expedia travel package?
With a travel package, you're in control. Whether you'd prefer to fly to Half Day in first class or coach, simply select from the available airline options. Expedia has access to more than 550 airline partners globally.

Stay near popular Half Day attractions

Marriott Theatre

9.0/10 (48 reviews)
You can enjoy a show at Marriott Theatre on your trip to 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

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Architecture River Tour from Michigan Avenue

Architecture River Tour from Michigan Avenue

£31
per adult
Architecture River Tour from Michigan Avenue
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. Flight-inclusive packages are ATOL protected.