Englewood Vacations from $376
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Your Englewood Vacation
Make travel planning stress-free by snapping up a vacation package to Englewood. Let us look after the minutiae, so you can concentrate on soaking up everything this neighborhood can offer. Hoping to sightsee during your trip to Englewood? Be sure to stop by nearby attractions such as University of Chicago, Robie House and 4944 S Woodlawn Ave. Don't just wish for it — do it! Book your perfect Englewood vacation with Expedia and travel your way.
The Latest Englewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $647, price is now $376 per person
$376
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Rooms were clean, staff was super friendly. Kind of wish there was a spa or gym but free breakfast was a nice touch. You cant beat the location.
Reviewed on Dec 28, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $820, price is now $466 per person
$466
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
The room was the perfect size and was very clean. The bed was a little hard, but other than that we loved our stay!
Reviewed on Dec 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,469, price is now $870 per person
$870
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Absolutely loved the hotel.Grand Dulxe Suite was huge with amazing views.All staff top notch.
Reviewed on Dec 27, 2025
Where to stay in Englewood
Find the best Englewood areas and neighborhoods for the activities you enjoy most. Learn more about 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.
Englewood Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 5 to Jan 6
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,592 reviews)
Easy check in and check out, staff were very friendly, room was great, bed was very comfortable. The hotel was also very clean. We loved the location. It was so close to Michigan Avenue, but it was quiet.
Reviewed on Dec 28, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $179 total per night from Jan 5 to Jan 6
$179 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.4/10 Very Good! (2,182 reviews)
Excellent stay, we loved it
Reviewed on Dec 27, 2025
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $173 total per night from Jan 5 to Jan 6
$173 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.4/10 Very Good! (2,424 reviews)
Overall very clean and very friendly staff
Reviewed on Dec 28, 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 Englewood
Michigan Avenue
4.5/5(332 reviews)
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.
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Chicago Bulls Basketball Game at United Center
$80
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
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- Chicago Vacations
- South Englewood Vacations
- Greater Salem Baptist Church
- Visit South Englewood
- Visit Washington Park
- Visit West Englewood
- DuSable Museum of African-American History
- Chicago Museum of Science and Industry
- Midway Plaisance
- Lorado Taft's Midway Studios
- Visit Greater Grand Crossing
- Visit Woodlawn
- University of Chicago
- Robie House
- Smart Museum of Art
- Rockefeller Memorial Chapel
- Visit Canaryville
- Hyde Park Vacations
- Visit Washington Park Court
- Visit New City
- Obama's House
- KAM Synagogue
- 4944 S Woodlawn Ave
- Visit Hyde Park
- Visit Fuller Park
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.