Drexel Estate Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place
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
Save 100% on your flight
Price was S$989, price is now S$696 per person
S$696
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,450 reviews)
I think this is a good hotel in an extremely convenient location whether you plan to walk or catch a ride. Close to everything and staff was pleasant.

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,791, price is now S$1,134 per person
S$1,134
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,043, price is now S$1,388 per person
S$1,388
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,206, price is now S$848 per person
S$848
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,382, price is now S$984 per person
S$984
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (2,837 reviews)
Property was well located to be able to explore Chicago easily. Very clean hotel and the staff was extremely accommodating. The only thing missing was a pool but it wasn’t a huge issue. Very nice hotel and would go back for sure.

Reviewed on 20 Aug, 2025

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
Downtown Chicago which includes a city

Downtown Chicago

5 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

Top hotels in Drexel Estate

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 S$228 per night from 1 Sept to 2 Sept
S$228
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug, 2025

The Wade
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 S$284 per night from 14 Sept to 15 Sept
S$284
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,026 reviews)
"Family had a great stay."

Reviewed on 21 Aug, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$230 per night from 3 Sept to 4 Sept
S$230
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,742 reviews)
"I loved the suite idea! The breakfast had a large and varied assortment and great dining area! The staff were obliging and convenient to text for additional towels or housekeeping! Although, trash pickup was noisy at 5am every morning facing the south toward the parking garage. Can you ask for a ..."

Reviewed on 21 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,676 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 S$696, 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.