Drexel Estate 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 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.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

CA $1,063
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,097 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,534
per person
Oct 20 - Oct 24
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,096
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,983
per person
Sep 14 - Sep 17
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Great staff, great place!

Reviewed on Aug 5, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,686
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (512 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 busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

Find hotels in The Loop
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Find hotels in Theatre District

Drexel Estate Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $146
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,961 reviews)
"I was double charged. Still trying to get resolved!!"

Reviewed on Aug 9, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $303
CA $356 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very good! (2,379 reviews)
"Go place to stay if your traveling and have a connection next day. Also very safe! A bit expensive especially the valet parking"

Reviewed on Aug 9, 2026

Hilton Chicago O'Hare Airport
See all 4,558 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
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Drexel Estate vacation package cost?
Perhaps less than you might think — from just CA $1,063, 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 $38
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 $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $70
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.