Drexel Estate Holidays

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    Save up to €900 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
€2,025
per person
1 Oct - 7 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
€2,308
per person
8 Oct - 14 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
€2,069
per person
8 Oct - 14 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.

Reviewed on 14 Aug 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
€2,059
per person
8 Oct - 14 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9/10 Wonderful! (3,779 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
€2,329
per person
6 Oct - 11 Oct
found 1 hour ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.6/10 Exceptional! (1,000 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.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top hotels in Drexel Estate

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€118
8 Sept - 9 Sept
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
€147
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,995 reviews)
"No microwave or free breakfast in the morning. No coffee or tea maker in the room. The walls are paper thin, so you can hear kids screaming and toilets flushing. The rooms aren’t properly cleaned, as we found a black spider in the bath towels."

Reviewed on 15 Aug 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
€244
12 Sept - 13 Sept
includes taxes & fees
8.4/10 Very good! (2,400 reviews)
"Clean room。nearly airport."

Reviewed on 14 Aug 2026

Hilton Chicago O'Hare Airport
See all 4,556 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.

Frequently asked questions

How much does a Drexel Estate holiday package cost?
Perhaps less than you might think — from just €2,025, as a matter of fact! By combining hotels, flights and car rentals into a custom-built holiday 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 holiday.
Where should I stay in Drexel Estate?
We recommend staying near the action. Many travellers 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 holiday?
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 holiday!
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 holiday 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 holiday 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 holiday 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

€24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
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.