Englewood Vacations from $240
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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.
Illinois Beach Hotel
Save 100% on your flight
Price was $409, price is now $240 per person
$240
per person
Feb 3 - Feb 8
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (478 reviews)
We had to switch rooms due to not having hot water but the staff was very good and switched us with no issues
Reviewed on Dec 20, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $760, price is now $418 per person
$418
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $595, price is now $329 per person
$329
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
This hotel was fantastic. Great location, great breakfast, clean, and although they don’t have onsite parking it was still available and convenient and cheaper than the rest. Will definitely be back!—10/10 for sure!
Reviewed on Dec 22, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $659, price is now $383 per person
$383
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
The room was awesome! The neighborhood was awesome but the real champs were the staff! Demetrius took extra special care of us for our special evening and it made it incredible!
We will absolutely be back anytime we’re in the city and if you want a clean, enjoyable, tentative stay this is the place to go to!
Reviewed on Dec 21, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $569 per person
$569
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!
Reviewed on Dec 21, 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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $174 total per night from Dec 29 to Dec 30
$174 total
Dec 29 - Dec 30
Total with taxes and fees
8.4/10 Very Good! (2,160 reviews)
The room and staff were wonderful.
Reviewed on Dec 21, 2025
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 5 to Jan 6
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,537 reviews)
Room was spotless, cleaned daily, no interruptions or negative situations. Great location, nice hotel, helpful staff. Recommend.
Reviewed on Dec 21, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,147 reviews)
Everything was top notch except the teeny tiny bed my husband and I had to share. We have a king bed at home. Not fun sharing a double. And we are not big people.
Reviewed on Dec 21, 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
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
Chicago Bulls Basketball Game at United Center
$80
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
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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
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- Visit New City
- Obama's House
- KAM Synagogue
- 4944 S Woodlawn Ave
- Visit Hyde Park
- Visit Fuller Park
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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.