Englewood Vacations from $342
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
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.
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
I stay there whenever I travel international. I fly back and forth several times a year. Before I take a domestic flight from O'Hare to my final destination, I stay overnight. I have always found the staff to be professional, accommodating and knowledgeable. The shuttle service and driver are excellent and the hotel has onsite dining as well as nearby off-site options.
Reviewed on Aug 18, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on Aug 17, 2025
Staybridge Suites Chicago O'Hare - Rosemont by IHG
O'Hare
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Good setup and facilities. Unfortunately very noisy - doors do not seal, adjoinjng rooms can hear each other clearly. Traffic, aircraft noise can be heard, and aircon is very loud.
Reviewed on Aug 17, 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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,965 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."
Reviewed on Aug 17, 2025
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,194 reviews)
"Staff was kind and friendly."
Reviewed on Aug 17, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$161 nightly
The price is $189 total per night from Sep 3 to Sep 4
$189 total
Sep 3 - Sep 4
Total includes taxes and fees
8.4/10 Very Good! (4,717 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"
Reviewed on Aug 17, 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
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 By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Cheap Hotels in Chicago
- Hotels near Halsted Station
- Hotels near 63rd Station
- Hotels near Garfield Station
- Hotels near Ashland-63rd Station
- Motels in Ashland-63rd Station
- Hotels near Greater Salem Baptist Church
- Hotels near Washington Park
- Hotels near King Drive Station
- 3 Star Hotels in Washington Park
- Motels in King Drive Station
- Hotels near West Englewood
- 3 Star Hotels in West Englewood
- Hotels near Drexel Estate
- 3 Star Hotels in Drexel Estate
- Hotels near Greater Grand Crossing
- 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 51st Station
- Hotels near Washington Park
- Hotels near Hyde Park
- Hotels near Cottage Grove Station
- Hotels near 47th Station
- Hotels near DuSable Museum of African-American History
- Hotels near Canaryville
- Hotels near Midway Plaisance
- Hotels near University of Chicago
- Hotels near Lorado Taft's Midway Studios
- Hotels near Auburn Park
- Hotels near Washington Park Court
- Hotels near New City
- 5 Star Hotels in New City
- Hotels near Renaissance Society
- Hotels near 47th Station
- Hotels near Bond Chapel
- Hotels near Nuclear Energy Sculpture
- Hotels near Court Theatre
- Southwest Side Hotels
- Hotels near Oak Woods Cemetery
- Hotels near 79th Station
- Cheap Hotels in Hyde Park
- Hotels near Smart Museum of Art
- Hilton Hotels in Hyde Park
- Hotels near Rockefeller Memorial Chapel
- Hotels near Oriental Institute Museum
- Marriott Hotels & Resorts in Hyde Park
- Hotels near Fuller Park
- 4 Star Hotels in Fuller Park
- 3 Star Hotels in Fuller Park
- Hyatt Hotels in Hyde Park
- 4 Star Hotels in Hyde Park
- Hotels with an Indoor Pool in Hyde Park
- Resorts & Hotels with Spas in Hyde Park
- Pet-friendly Hotels in Hyde Park
- 5 Star Hotels in Hyde Park
- Motel 6 Hotels in Hyde Park
- Luxury Hotels in Hyde Park
- Extended Stay America Hotels in Hyde Park
- Hotels with Kitchenettes in Hyde Park
- 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
- Car rentals near Chicago
- Car rentals near Woodlawn
- Car rental Chicago Airport (MDW)
- Car rentals near University of Chicago
- Car rentals near Nuclear Energy Sculpture
- Standard Car Rentals near University of Chicago
- Car rentals near Hyde Park
- Enterprise Rental Cars in Hyde Park
- Hertz Rental Cars in Hyde Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.