Englewood Vacations from $314
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $595, price is now $314 per person
$314
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast, Clean room, enjoyed the stay
Reviewed on Jan 9, 2026
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $682, price is now $353 per person
$353
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $839, price is now $470 per person
$470
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $696, price is now $410 per person
$410
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
The room was spacious and the amenities great.
Food was good both at the cafe and in the restaurant.
Good location
Reviewed on Jan 9, 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
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 19 to Jan 20
$192 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (2,510 reviews)
Staff members were friendly and helpful. Great location walking distance and transportation options.
Reviewed on Jan 9, 2026
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 18 to Jan 19
$105 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (3,677 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...
Reviewed on Jan 7, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Jan 30 to Jan 31
$103 total
Jan 30 - Jan 31
Total with taxes and fees
8.6/10 Excellent! (2,048 reviews)
Pedro and front office staff made our stay excellent. Return customer love the location, room quality and value overall. Room size and features make this our first choice in the city
Reviewed on Jan 7, 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
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.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
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.