Homewood Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

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

Homewood Holiday

Our pick of the best Homewood Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$276 per night from 22 July to 23 July
NZ$276
22 July - 23 July
includes taxes & fees
8.2/10 Very good! (1,030 reviews)
"I had a TERRIBLE experience at a stinking Extended Stay and needed a last minute room. This hotel was excellent. I booked the room here, and checked in within 20 minutes. The room was clean and the housekeeper was outstanding. Thank you."

Reviewed on 10 July 2026

Holiday Inn Chicago – Midway Airport S by IHG
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
The price is NZ$135 per night from 29 July to 30 July
NZ$135
29 July - 30 July
includes taxes & fees
6.4/10 (1,187 reviews)
"The employees are very friendly and very clean rooms 10/10"

Reviewed on 7 July 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$243 per night from 28 July to 29 July
NZ$243
28 July - 29 July
includes taxes & fees
8/10 Very good! (1,980 reviews)
"It was okay. Not terrible, not filthy, there's really no amenities there. For the price. It's not a bad stay."

Reviewed on 10 July 2026

Sleep Inn Midway Airport Bedford Park
See all 990 properties in Homewood
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.

Stay near popular Homewood attractions

Ravisloe Country Club

7.6/10 (4 reviews)
This Donald Ross-designed golf course challenges players with its rolling mounds and deep bunkers. Experience classic golfing on meticulously maintained greens, then enjoy a meal at the elegant clubhouse.
See properties

What to do in Homewood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$48
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$70
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Homewood

Frequently asked questions

How much does a Homewood holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday to Homewood costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Homewood?
January, June and September are the best times to look for cheap Homewood holiday packages. Travelling in less busy periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Homewood?
Typically, a handful of days is enough to explore the main attractions during your Homewood holiday. However, if you'd like to have some time to unwind or take day tours, consider extending your trip.
How to find the best Homewood package deals?
Bagging a cheap Homewood package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Homewood package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Homewood holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a tailored Homewood holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Homewood?
If you're planning a spur-of-the-moment Homewood getaway, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Homewood?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the available activities will also help you decide when to escape to Homewood.
  2. Budget wisely: Besides the cost of your stay, you should consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Homewood.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you want to experience in Homewood. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalised Homewood holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.