Winfield Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Winfield

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 S$186 per night from 4 Jul to 5 Jul
S$186
4 Jul - 5 Jul
includes taxes & fees
8.6/10 Excellent! (1,618 reviews)
"Cleanness"

Reviewed on 10 Jun, 2025

Hyatt Regency O'Hare Chicago
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 S$345 per night from 4 Jul to 5 Jul
S$345
4 Jul - 5 Jul
includes taxes & fees
8/10 Very Good! (2,063 reviews)
Handy in a pinch
"My flight home was cancelled due to storms and I needed a place to stay for the night. While not the most affordable option, it was nice to stay right at the airport under these circumstances. The fancy restaurant on the lower level was good. The staff was very helpful."

Reviewed on 10 Jun, 2025

Hilton Chicago O'Hare Airport
Grand Royal Hotel O'Hare - Chicago
Grand Royal Hotel O'Hare - Chicago
3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is S$92 per night from 23 Jun to 24 Jun
S$92
23 Jun - 24 Jun
includes taxes & fees
5.2/10 (66 reviews)
"First part of our trip wasn't good, after flying from Sacramento, CA to Chicago, IL for my college graduation we went to check into Extended Stay and waited for 35 minutes to see if they had a room for me or not. The next hotel that we we're able to check into right away. We wasted $54 on an uber ..."

Reviewed on 9 Jun, 2025

Grand Royal Hotel O'Hare - Chicago
See all 1,270 properties in Winfield
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 Winfield holiday package cost?
You’ll find cheap prices on Expedia for your Winfield getaway. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Winfield costs.
What are the cheapest months to go to Winfield?
Travel in the off-season and you’re likely to find cheap Winfield holiday packages. Bear in mind that public holidays and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Winfield?
The ideal length for your Winfield holiday depends on what you’d like to see. Usually, a few days to a week will give you time to hit all the main attractions and explore some hidden treasures along the way.
How to find the best Winfield package deals?
Start your search for a Winfield package deal by entering your preferred travel dates and destination under our “Packages” tab. Then add a few filters, like “Property type” and “Popular locations,” to fine-tune the results to your exact style. You can also sort by “Package discount” and discover offers that come with unbeatable savings. If you don’t find the ideal Winfield package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winfield adventure underway.
Is it cheaper to book a Winfield holiday as a package?
You can enjoy significant savings on your next Winfield break by booking a tailored holiday package. Check the “Package” heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winfield?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winfield break.
How to plan a trip to Winfield?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Winfield.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to set aside for your trip to Winfield. Then, select a property that suits your budget, whether that’s an economical stay or a high-end retreat.
  3. Determine how many days away: Start by making a list of all the attractions you’d like to experience in Winfield. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that’s left is to pick a Winfield holiday package that brings all your bookings together.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Winfield

River tour boat in Chicago

Architecture River Tour

S$63
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$43
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Winfield

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.