Glencoe Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Glencoe Vacation

A great way to experience this city is with a custom-made Glencoe vacation package. Base yourself in the neighborhood of Rogers Park, which is great for cafes, nature and bars and pubs or go someplace else — our packages are all about you. Make your trip to Glencoe even more fulfilling by including some sightseeing. Chicago Botanic Garden, The Glen Club and North Shore Center for the Performing Arts are some of the top attractions you'll want to explore. Check out Expedia's wide range of travel options and start planning your perfect vacation to Glencoe now.

Top Glencoe Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,195, price is now CA $942 per person
CA $942
per person
Jan 21 - Jan 24
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,321, price is now CA $978 per person
CA $978
per person
Jan 21 - Jan 24
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,324, price is now CA $1,004 per person
CA $1,004
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Very walkable to Michigan Avenue with chic modern designs in a vintage building. Friendly staff. Stayed for one night, very comfortable and clean room.

Reviewed on Nov 6, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,731, price is now CA $1,315 per person
CA $1,315
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
Beautiful rooms and service.

Reviewed on Nov 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,457, price is now CA $1,902 per person
CA $1,902
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint

Reviewed on Nov 6, 2026

Ready to book your vacation to Glencoe?

 

Choose your dates

Glencoe Hotel Deals

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 CA $162 per night from Nov 23 to Nov 24
CA $162
CA $193 total
Nov 23 - Nov 24
includes taxes & fees
8/10 Very good! (10,108 reviews)
"Beautiful hotel. Asked for adjoining rooms and was accommodated. Comfortable beds and pillows. Would stay again."

Reviewed on Nov 6, 2026

Congress Plaza Hotel
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 $162 per night from Nov 9 to Nov 10
CA $162
CA $193 total
Nov 9 - Nov 10
includes taxes & fees
8/10 Very good! (2,668 reviews)
"Nice area"

Reviewed on Nov 6, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundable
The price is CA $154 per night from Nov 15 to Nov 16
CA $154
CA $183 total
Nov 15 - Nov 16
includes taxes & fees
8.8/10 Excellent! (5,584 reviews)
"Great location. Staff was welcoming. Room was perfect"

Reviewed on Nov 6, 2026

River Hotel
See all 4,221 properties in Glencoe
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Glencoe attractions

Writers Theatre

You can enjoy a show at Writers Theatre during your stay in Glencoe. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

What to do in Glencoe

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Glencoe

Frequently asked questions

How much does a Glencoe vacation package cost?
You can snap up a vacation package to this top destination from CA $942 on Expedia. However, how much your vacation to Glencoe costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Glencoe?
If you're looking to score a cheap Glencoe vacation package, consider visiting in January, February and November. You're likely to find better rates on accommodations and flights during these months — ideal for budget-conscious travellers.
How many days is enough for Glencoe?
With about 2 days, you'll have enough time to enjoy popular neighbourhoods like Gross Point and Highwood during your Glencoe vacation. Make sure to also add The Glen Club and Baha'i House of Worship to your list of must-sees. Up for some more adventures? Consider venturing outside of Glencoe on tours and day trips.
How to find the best Glencoe package deals?
Bagging a cheap Glencoe package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Glencoe package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Glencoe vacation as a package?
You can enjoy significant savings on your Glencoe escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Glencoe?
If you're planning an impromptu Glencoe getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Glencoe?

  1. Pick your dates: The things you plan to do in Glencoe and your preferred season can help you decide when to go.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Glencoe. Then, pick a property that suits your budget, whether that's an affordable option or a high-end retreat.
  3. Decide your trip length: Consider how long you want to spend discovering Glencoe. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Glencoe vacation package.

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