Drexel Estate Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Drexel Estate Vacation

The best way to experience this unique city is with a customized Drexel Estate vacation package. Stay in the neighborhood of Magnificent Mile, which is good for cafes, shopping and history or go someplace else — our packages are all about you. If your trip to Drexel Estate includes some sightseeing, visit famous attractions like Marquette Park, S.S. Peter and Paul Church and Balzekas Museum of Lithuanian Culture. Expedia can help you escape the everyday. Tailor your vacation to Drexel Estate to suit your travel style, whatever that may be!

Top Holiday Package Deals in Drexel Estate

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,794, price is now CA $1,126 per person
CA $1,126
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.

Reviewed on Nov 13, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $4,165, price is now CA $2,806 per person
CA $2,806
per person
Jan 22 - Jan 25
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 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 $1,820, price is now CA $1,271 per person
CA $1,271
per person
Jan 22 - Jan 25
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Where to stay in Drexel Estate

Find the best Drexel Estate areas and neighborhoods for the activities you enjoy most. Learn more about Drexel Estate
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Drexel Estate 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 $166 per night from Nov 22 to Nov 23
CA $166
CA $197 total
Nov 22 - Nov 23
includes taxes & fees
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 $165 per night from Dec 1 to Dec 2
CA $165
CA $197 total
Dec 1 - Dec 2
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Dec 15 to Dec 16
CA $141
CA $168 total
Dec 15 - Dec 16
includes taxes & fees
8.8/10 Excellent! (5,617 reviews)
"Amazing spot right in the middle of the action, shopping to the north and attractions to the south. The river right beside the hotel and the lake a short walk away. My room was a little tight but I am not in Chicago to be in my room. Would stay here again in a heartbeat."

Reviewed on Nov 14, 2026

River Hotel
See all 4,537 properties in Drexel Estate
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
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Family Vacations

Frequently asked questions

How much does a Drexel Estate vacation package cost?
Perhaps less than you might think — from just CA $1,126, as a matter of fact! By combining hotels, flights and car rentals into a custom-built vacation package, your trip to Drexel Estate is just clicks away.
How do I get a cheap travel package to Drexel Estate?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all covered. Pick a combination that suits you and watch your savings pile up. Of course, a travel package is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 properties across the world, which lets you customize your Drexel Estate vacation.
Where should I stay in Drexel Estate?
We recommend staying near the action. Many travelers like to book hotels in the vicinity of top attractions, like Marquette Park, St. Bernard Hospital and Balzekas Museum of Lithuanian Culture.
How far in advance should I book my Drexel Estate vacation?
Reward yourself with the widest variety and the lowest prices by booking your Drexel Estate adventure early. Air carriers tend to publish tickets anywhere up to a year prior to departure, so start locking things in ASAP. Having said that, Expedia is constantly working to give you the best deals around, so it's never a bad time to book your dream vacation!
What does an Expedia Drexel Estate travel package include?
Expedia has everything you need to book your Drexel Estate trip, but how you structure your package is up to you. Pick from any combination of hotels, flights and rental cars. Searching for some tours or experiences to keep you on the move? Once you've made your booking, you can add them on too. Whatever your budget, there's a package deal to meet your needs.
What should I know before booking a Drexel Estate travel package?
A travel package can be customized for your budget and is a great way to make your budget go further. What you include is completely up to you. Hotels, rental cars and flights — decide on a combination that suits your plans.
Can I choose my airline with a Drexel Estate Expedia vacation package?
Yes, the choice is yours. We offer more than 550 partner airlines all over the world, so you can tailor your Drexel Estate adventure according to your budget and travel needs.
If I'm not able to travel, can I cancel my Drexel Estate vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. To learn more, visit our Customer Service Portal. But generally speaking, if you've booked your Drexel Estate vacation package in the last 24 hours, you may be able to change or cancel it without penalty. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Things to do

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
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $71
per adult
92% of travellers recommend
Chicago By Night River and Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.