Mount Greenwood Holidays from NZ$2,866

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

The Latest Mount Greenwood Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,767, price is now NZ$2,866 per person
NZ$2,866
per person
29 Oct - 5 Nov
found 6 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on 21 Aug. 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$4,134, price is now NZ$3,085 per person
NZ$3,085
per person
29 Oct - 5 Nov
found 6 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug. 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was NZ$5,770, price is now NZ$4,323 per person
NZ$4,323
per person
29 Oct - 5 Nov
found 6 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$4,142, price is now NZ$3,126 per person
NZ$3,126
per person
29 Oct - 5 Nov
found 6 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
I enjoyed the total experience of staying at this facility.

Reviewed on 22 Aug. 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was NZ$3,786, price is now NZ$2,934 per person
NZ$2,934
per person
29 Oct - 5 Nov
found 6 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
8.4/10 Very Good! (1,872 reviews)
Always love staying at The Palmer. The location is super convenient and the property oozes with Chicago charm. The staff is kind and always willing to help. Looking forward to my next stay.

Reviewed on 23 Aug. 2025

Mount Greenwood Holiday

Our pick of the best Mount Greenwood Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$302 per night from 1 Sept to 2 Sept
NZ$302
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug. 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$376 per night from 14 Sept to 15 Sept
NZ$376
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug. 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 3 Sept to 4 Sept
NZ$304
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on 23 Aug. 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,455 properties in Mount Greenwood
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.

Discover the most popular places to visit in Mount Greenwood

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

Wrigley Field

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

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

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 Mount Greenwood

River tour boat in Chicago

Architecture River Tour

NZ$69
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$75
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$68
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Mount Greenwood

Frequently asked questions

What are the cheapest months to go to Mount Greenwood?
You're likely to find lower prices and greater availability in January, February and November. Check out our cheap Mount Greenwood holiday packages and you could score some excellent off-season deals.
How many days is enough for Mount Greenwood?
The ideal duration for your Mount Greenwood holiday depends on what you'd like to see and do. Generally, a handful of days to a week will give you plenty of time to go to all the major attractions and discover some hidden treasures along the way.
How to find the best Mount Greenwood package deals?
Landing a cheap Mount Greenwood package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can customise your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Mount Greenwood package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
When to book a holiday package to Mount Greenwood?
If you've got your Mount Greenwood holiday dates locked in, book early to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Mount Greenwood?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to visit Mount Greenwood.
  2. Set a budget: Consider costs like food, flights and transportation when calculating how much to put aside for your trip to Mount Greenwood. Then, pick a hotel that works with your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Mount Greenwood. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Mount Greenwood holiday package that brings all your bookings together.

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