Englewood Vacations from $237
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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.
Holiday Inn Chicago - Schaumburg by IHG
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
16.4/10 Exceptional! (999 reviews)
Rooms were clean and overall the hotel was nice
Reviewed on Nov 1, 2025
Level Chicago – Old Town
Downtown Chicago
Price was $3,257, price is now $1,529 per person
$1,529
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
The Westin Michigan Avenue Chicago
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $486 per person
$486
per person
Dec 20 - Dec 23
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025
The Godfrey Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $597, price is now $356 per person
$356
per person
Feb 2 - Feb 9
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
17.2/10 Exceptional! (1,887 reviews)
Clean room staff was amazing and helpful
Reviewed on Nov 19, 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
4 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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Dec 8 to Dec 9
$103 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (5,272 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.
Reviewed on Nov 19, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $149 total per night from Nov 26 to Nov 27
$149 total
Nov 26 - Nov 27
Total with taxes and fees
8.4/10 Very Good! (2,065 reviews)
Classy and classic! Never disappoints
Reviewed on Nov 16, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,324 reviews)
Awesome location and valet was very helpful
Reviewed on Nov 18, 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
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
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
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Explore a world of travel with Expedia
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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
- Car rentals near Chicago
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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.