Englewood Vacations from $229
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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.
Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
Price was $409, price is now $229 per person
$229
per person
Feb 7 - Feb 11
found 2 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
15.2/10 Exceptional! (1,002 reviews)
Clean rooms, great location in Evanston near the university. Helpful staff.
Reviewed on Nov 17, 2025
The Emily Hotel
Downtown Chicago
Price was $1,702, price is now $814 per person
$814
per person
Jan 24 - Jan 26
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe.
Reviewed on Nov 22, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $680 per person
$680
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.
Reviewed on Nov 25, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $927, price is now $500 per person
$500
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (1,002 reviews)
The Chicago Athletic Association Hotel is the most charming hotel in the city of Chicago. My wife and I recently got married in Chicago and one of the highlights of the weekend was hanging out at the hotel! It has a roaring 20's vibe with the dark woods in the main lobby and the large game room which is a fun place to get a drink and play chess/pool. Amazing location close to the Amtrak, Chicago subway, and the South shore railroad. And it's across the street from Millennium Park. Most importantly, the staff is very professional and attentive and will go above and beyond to make your stay perfect. I always stay at this hotel when I go to Chicago because of it's charm and service. I would never stay anywhere else because it's a truly unique hotel in an awesome location with the nicest and most professional staff. 10/10 recommend to anyone!
Reviewed on Nov 20, 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
$136 nightly
The price is $155 total per night from Dec 21 to Dec 22
$155 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,096 reviews)
Beautiful hotel, lovely staff. An experience you don’t want to miss.
Reviewed on Nov 25, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$87 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (5,291 reviews)
All above.
Reviewed on Nov 24, 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! (3,372 reviews)
Rooms are spotless and front desk service amazing. Cleaning room service very kind and friendly.
Reviewed on Nov 25, 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
96% 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
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- Chicago Vacations
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- Greater Salem Baptist Church
- Visit South Englewood
- Visit Washington Park
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- DuSable Museum of African-American History
- Chicago Museum of Science and Industry
- Midway Plaisance
- Lorado Taft's Midway Studios
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- 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
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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.