Winfield Holidays from NZ$2,542

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The Latest Winfield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (3,410 reviews)
It was a convenient location and very clean. Would be nice if they offered a small breakfast for free.

Reviewed on 21 Jun. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Great hotel with great staff.

Reviewed on 20 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,039 reviews)
I overall liked staying at the Riu. However, the shower and sink water pressure was too weak. Also, the two sinks wasted space that could have been used for personal items.

Reviewed on 21 Jun. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 Jun. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,087 reviews)
Great setup, location

Reviewed on 21 Jun. 2025

Winfield Holiday

Our pick of the best Winfield Hotel Deals

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 NZ$258 per night from 4 July to 5 July
NZ$258
4 July - 5 July
includes taxes & fees
8.6/10 Excellent! (1,643 reviews)
"I like the spacious and clean shower room in the hotel. Very good 👍"

Reviewed on 21 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 NZ$376 per night from 19 July to 20 July
NZ$376
19 July - 20 July
includes taxes & fees
8/10 Very Good! (2,060 reviews)
"Nice hotel…convenient to airport terminals 1, 2 & 3 either by shuttle or underground passages. It’s a bit of a hike from the international terminal…shuttle may be the best option if you have much luggage. Our room was very quiet - unlike many airport hotels."

Reviewed on 21 Jun. 2025

Hilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is NZ$213 per night from 26 June to 27 June
NZ$213
26 June - 27 June
includes taxes & fees
8.6/10 Excellent! (2,221 reviews)
"Close to shopping"

Reviewed on 21 Jun. 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,281 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 from NZ$2,542 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.

Discover the most popular places to visit in Winfield

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

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

4.5/5(21 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

NZ$81
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

NZ$75
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$74
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.