Englewood Vacations from $244
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 Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $424, price is now $244 per person
$244
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.
Reviewed on Feb 2, 2026
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $884, price is now $502 per person
$502
per person
Apr 30 - May 3
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $989, price is now $593 per person
$593
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Service was amazing and the location was perfect. Would definitely stay here again.
Reviewed on Jan 28, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $564, price is now $347 per person
$347
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 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
$95 nightly
The price is $112 total per night from Feb 10 to Feb 11
$112 total
Feb 10 - Feb 11
Total with taxes and fees
8/10 Very Good! (9,853 reviews)
Friendly staff. Clean room.
Reviewed on Feb 5, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $240 total per night from Mar 1 to Mar 2
$240 total
Mar 1 - Mar 2
Total with taxes and fees
8.2/10 Very Good! (2,215 reviews)
A very good value. A bit worn, great bed but half the price of the Westin Denver airport.
Reviewed on Feb 8, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $120 total per night from Feb 22 to Feb 23
$120 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless
Reviewed on Feb 4, 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
$166
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% 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
- 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.