Mount Greenwood Vacation Packages

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Top Mount Greenwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,051, price is now CA $760 per person
CA $760
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
Friendly staff and rooms are very clean and well maintained

Reviewed on Jul 17, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,169, price is now CA $1,554 per person
CA $1,554
per person
Aug 24 - Aug 28
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Level hotels are awesome

Reviewed on Jul 18, 2026

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 CA $2,518, price is now CA $1,807 per person
CA $1,807
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,551, price is now CA $1,123 per person
CA $1,123
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)
Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!

Reviewed on Jul 17, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,652, price is now CA $1,208 per person
CA $1,208
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)

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Mount Greenwood Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from Jul 27 to Jul 28
CA $272
CA $323 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,775 reviews)
"The location is great, the cleanliness is appreciated and the staff are very helpful. The noise from AC was a bit annoying, but the overall experience was great."

Reviewed on Jul 18, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 CA $419 per night from Aug 9 to Aug 10
CA $419
CA $498 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,927 reviews)
"Well... when we got there the rooms weren't ready and we had to wait over 4 hours until we finally got our rooms ready at 9 pm. There was no water in my room. And the room AC was very loud and the constant elevator noise while it moved up and down throughout the night... felt like sleeping next to ..."

Reviewed on Jul 18, 2026

The Wade
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $380 per night from Jul 26 to Jul 27
CA $380
CA $498 total
Jul 26 - Jul 27
includes taxes & fees
Omni Chicago Hotel
See all 4,227 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.
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What to do in Mount Greenwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Mount Greenwood

Frequently asked questions

How much does a Mount Greenwood vacation package cost?
Offering excellent value package deals from CA $760 on Expedia, you'll be surprised at how little a vacation to Mount Greenwood costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Mount Greenwood?
January, February and November are the best times to search for cheap Mount Greenwood vacation packages. Choosing to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Mount Greenwood?
With about 2 days, you'll have plenty of time to enjoy popular neighbourhoods such as Ashburn and Merrionette Park during your Mount Greenwood vacation. Make sure to also add Lake Katherine Nature Centre and Hollywood Park to your sightseeing list. In the mood for more adventures? Consider exploring outside of Mount Greenwood on day trips and tours.
How to find the best Mount Greenwood package deals?
Finding a cheap Mount Greenwood package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Mount Greenwood 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 often lower.
Is it cheaper to book a Mount Greenwood vacation as a package?
You can enjoy significant savings on your next Mount Greenwood escape by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Mount Greenwood?
If you have your Mount Greenwood travel dates finalized, book as soon as you can to score some outstanding deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Mount Greenwood?

  1. Pick your dates: What you want to do in Mount Greenwood and your favourite season will help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Mount Greenwood.
  3. Decide how long to go away for: Now that you're up to speed on Mount Greenwood, you can work out the perfect length of your vacation. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Mount Greenwood vacation 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.