Englewood Vacations from $359
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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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $663, price is now $359 per person
$359
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Room was extremely clean, and staff was very accommodating
Reviewed on Jan 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $756, price is now $383 per person
$383
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean, spacious room. Great breakfast and hospitality.
Reviewed on Jan 19, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was $1,719, price is now $904 per person
$904
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $942, price is now $515 per person
$515
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!
Reviewed on Jan 10, 2026
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $806, price is now $466 per person
$466
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,059 reviews)
Besides the ambience and location of this gorgeous hotel... we enjoyed winding down the evening with a drink and Bertha's brownie in the lobby/lounge.
Reviewed on Jan 18, 2026
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $102 total per night from Jan 24 to Jan 25
$102 total
Jan 24 - Jan 25
Total with taxes and fees
8/10 Very Good! (9,790 reviews)
Really interesting place, great price for the location too. Staff was very friendly.
Reviewed on Jan 19, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $182 total per night from Feb 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (2,543 reviews)
Great. Did not put us in king size bed as ordered. Did not have washcloths/makeup cloths. They fixed all upon asking. Great service overall. Would stay again.
Reviewed on Jan 18, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$111 nightly
The price is $130 total per night from Feb 1 to Feb 2
$130 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (5,567 reviews)
room was emaculate and the staff were excellent as always
Reviewed on Jan 19, 2026
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
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
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Chicago Blackhawks Ice Hockey Game at United Center
$67
per adult
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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
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- University of Chicago
- Robie House
- Smart Museum of Art
- Rockefeller Memorial Chapel
- Visit Canaryville
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- Visit New City
- Obama's House
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- 4944 S Woodlawn Ave
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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.