Drexel Estate Vacations from $274

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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.
Holiday Inn Express & Suites Zion by IHG

Holiday Inn Express & Suites Zion by IHG

2.5 out of 5
Save 100% on your flight
Price was $392, price is now $274 per person
$274
per person
Apr 23 - Apr 27
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (186 reviews)
Staff was Excellent! Room was super clean!

Reviewed on Feb 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,409, price is now $862 per person
$862
per person
May 26 - May 30
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Interesting property in that it is a high rise building of furnished suites with certain floors available as a “hotel”. Coffee shop, gym and lounge are all nice as are the suites. Just know this is not a service oriented hotel experience. No doorman, uniformed person at desk, room or maid service etc.

Reviewed on Mar 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $677, price is now $415 per person
$415
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
I had a wonderful stay at Riu Plaza Chicago. Even though I live in Chicago, I wanted a nice staycation and this hotel did not disappoint. The rooms were very clean, comfortable, and the staff was welcoming and professional. The breakfast was also great with a good variety of options to choose from. Overall, I had a great time and really enjoyed my stay. I would definitely recommend this hotel and would stay again!

Reviewed on Mar 16, 2026

Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $805, price is now $532 per person
$532
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8/10 Very Good! (503 reviews)
Pool was out of commission. Front desk was welcoming.

Reviewed on Mar 5, 2026

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Save 100% on your flight
Price was $796, price is now $561 per person
$561
per person
May 21 - May 24
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
9.4/10 Exceptional! (278 reviews)
The room was very clean but the lighting in the room is very dark.

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

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

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
$106 nightly
The price is $124 total per night from Apr 1 to Apr 2
$124 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,948 reviews)
Hot water pressure was very very low. Had to leave the shower running for an hour turn it off completely then turn it back on for the pressure to work.

Reviewed on Mar 16, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Apr 6 to Apr 7
$179 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,543 reviews)
Staff was amazing, we were sad to go was fancier than I was used to. So many items required room key to function but i caught on and not feeling judged by not being sure what to do was appreciated.

Reviewed on Mar 16, 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
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Mar 23 to Mar 24
$153 total
Mar 23 - Mar 24
Total with taxes and fees
8.6/10 Excellent! (5,750 reviews)
Clean room

Reviewed on Mar 16, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,735 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$26
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
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.