South Englewood Vacations from $372
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 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
The Latest South Englewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Chicago/Alsip
Save 100% on your flight
Price was $585, price is now $372 per person
$372
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
8/10 Very Good! (1,006 reviews)
My stay was pretty good, staff were very friendly, and the hotel room was clean. I didn’t indulge in the complimentary breakfast, however, it smelled good every morning. Unfortunately, the walls are pretty thin and you can hear everything. Some guests smelled like weed even though marijuana is prohibited. Also a very few guests were playing loud music and walking up and down the hallway. My only advice would be to be careful since anybody can book a stay there.
Reviewed on Sep 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,110, price is now $1,258 per person
$1,258
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep 2, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $751 per person
$751
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
Great hotel, especially for the price, nice area, would go back again if I’m in Chicago.
Reviewed on Sep 2, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,086, price is now $705 per person
$705
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Excellent breakfast with a lot of options.
Reviewed on Sep 1, 2025
Where to stay in South Englewood
Find the best South Englewood areas and neighborhoods for the activities you enjoy most. Learn more about South Englewood
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.
South Englewood Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $200 total per night from Sep 4 to Sep 5
$200 total
Sep 4 - Sep 5
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$183 nightly
The price is $215 total per night from Sep 22 to Sep 23
$215 total
Sep 22 - Sep 23
Total with taxes and fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $196 total per night from Sep 22 to Sep 23
$196 total
Sep 22 - Sep 23
Total with taxes and fees
8.2/10 Very Good! (1,156 reviews)
"I enjoyed the location"
Reviewed on Aug 29, 2025
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.
Discover the most popular places to visit in South Englewood
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Hotels near Greater Salem Baptist Church
- Hotels near Halsted Station
- Hotels near Auburn Park
- Hotels near West Englewood
- 3 Star Hotels in West Englewood
- Hotels near Englewood
- 4 Star Hotels in Englewood
- Hotels near 63rd Station
- Hotels near Greater Grand Crossing
- Cheap Hotels in Chicago
- Hotels near Ashland-63rd Station
- Motels in Ashland-63rd Station
- Hotels near 79th Station
- Hotels near Drexel Estate
- 3 Star Hotels in Drexel Estate
- Hotels near Auburn Gresham
- Hotels near King Drive Station
- Motels in King Drive Station
- Motels in Chicago Gresham Station
- Hotels near Woodlawn
- La Quinta Inn & Suites Hotels in Woodlawn
- 5 Star Hotels in Woodlawn
- 4 Star Hotels in Woodlawn
- Omni Hotels in Woodlawn
- Hotels near Garfield Station
- Hotels near Cottage Grove Station
- Hotels near Washington Park
- Hotels near 87th Station
- Motels in 87th Station
- 3 Star Hotels in Washington Park
- Hotels near Oak Woods Cemetery
- Hotels near Chicago Brainerd Station
- Hotels near Chatham
- 5 Star Hotels in Chatham
- 4 Star Hotels in Chatham
- Hotels near Hyde Park
- Hotels near Midway Plaisance
- Hotels near Lorado Taft's Midway Studios
- Hotels near Chicago Lawn
- Hotels near Chicago 75th Street Station
- Hotels near University of Chicago
- Hotels near DuSable Museum of African-American History
- Hotels near Chicago 79th Street Station
- Hotels near ETA Creative Arts Foundation
- Hotels near Washington Park
- Hotels near Renaissance Society
- Hotels near Bond Chapel
- Hotels near Chicago 83rd Street Station
- Hotels near Chicago Stony Island Station
- Hotels near 51st Station
- Hotels near Essex
- Gay friendly Hotels in Essex
- Hilton Hotels in Essex
- Hotels near Chicago 91st Street Station
- Motels in Chicago 91st Street Station
- Southwest Side Hotels
- Hotels near Princeton Park
- Hotels near Rockefeller Memorial Chapel
- Hotels near Chicago 63rd Street Station
- Hotels near Nuclear Energy Sculpture
- Hotels near Marquette Park
- Greater Salem Baptist Church
- Chicago Vacations
- Visit West Englewood
- Visit Englewood
- Visit Greater Grand Crossing
- Chicago Museum of Science and Industry
- Visit Woodlawn
- Midway Plaisance
- Lorado Taft's Midway Studios
- DuSable Museum of African-American History
- Visit Chatham Fields
- ETA Creative Arts Foundation
- Visit Washington Park
- University of Chicago
- Robie House
- Rockefeller Memorial Chapel
- Visit Chatham
- Visit Chicago Lawn
- Smart Museum of Art
- Hyde Park Vacations
- Visit Essex
- Visit Princeton Park
- Cook County Vacations
- Car rentals near Chicago
- Car rentals near Gresham
- Car rentals near Auburn Gresham
- Car rentals near Woodlawn
- Car rentals near Chatham Fields
- Car rental Chicago Airport (MDW)
- Car rentals near Garden Homes
- Car rentals near Chatham
- Car rentals near University of Chicago
- Standard Car Rentals near University of Chicago
- Car rentals near Essex
- Car rentals near Nuclear Energy Sculpture
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.