Drexel Estate Vacations from $269

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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!

The Latest Drexel Estate Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $431, price is now $269 per person
$269
per person
May 5 - May 9
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (503 reviews)
Was an wonderful experience. The staff was very kind and helpful. The view was amazing. Highly recommend any time of the year!

Reviewed on Jan 12, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $862, price is now $514 per person
$514
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $571, price is now $370 per person
$370
per person
May 8 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great location , great service at the Bar.

Reviewed on Mar 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $877, price is now $572 per person
$572
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,136 reviews)
Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries.

Reviewed on Mar 1, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $707, price is now $471 per person
$471
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,266 reviews)
We loved are stay at the Thompson hotel. It's very clean, and is close to our favorite shops and restaurants.

Reviewed on Mar 2, 2026

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 showing a city

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

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
$101 nightly
The price is $118 total per night from Mar 4 to Mar 5
$118 total
Mar 4 - Mar 5
Total with taxes and fees
8/10 Very Good! (9,905 reviews)
Good

Reviewed on Mar 2, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$132 nightly
The price is $155 total per night from Mar 4 to Mar 5
$155 total
Mar 4 - Mar 5
Total with taxes and fees
9.4/10 Exceptional! (3,444 reviews)
Great location , great service at the Bar.

Reviewed on Mar 3, 2026

Hotel Riu Plaza Chicago
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
$110 nightly
The price is $130 total per night from Mar 5 to Mar 6
$130 total
Mar 5 - Mar 6
Total with taxes and fees
8.6/10 Excellent! (5,711 reviews)
Love the hotel just wish the pool water was warmer

Reviewed on Mar 2, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,824 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Drexel Estate

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in 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.