Englewood Vacations from $744
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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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,141, price is now $744 per person
$744
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,699, price is now $1,038 per person
$1,038
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Excellent customer service, amazing staff!
Reviewed on Jul 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,194, price is now $1,429 per person
$1,429
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Me encantó volveria mil veces a ese hotel
Reviewed on Jul 4, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,322, price is now $875 per person
$875
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 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
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $159 total per night from Jul 6 to Jul 7
$159 total
Jul 6 - Jul 7
Total with taxes and fees
8.2/10 Very Good! (1,689 reviews)
"We like our room, very clean and spacious"
Reviewed on Jul 4, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $144 total per night from Jul 6 to Jul 7
$144 total
Jul 6 - Jul 7
Total with taxes and fees
8/10 Very Good! (10,157 reviews)
"Great location- good price for a holiday weekend"
Reviewed on Jul 4, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $207 total per night from Jul 8 to Jul 9
$207 total
Jul 8 - Jul 9
Total with taxes and fees
9.2/10 Wonderful! (1,846 reviews)
"Great staff"
Reviewed on Jul 5, 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Explore a world of travel with Expedia
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- Mccormick Tribune Center
- Obama's House
- Lincoln Park Conservatory
- Goodman Theater
- Chicago Loop Synagogue
- United Center
- Chicago Symphony Orchestra
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- St. Basil Greek Orthodox Church
- Mary Bartelme Park
- Daley Plaza
- Chicago Vacations
- Buckingham Fountain
- Chicago Architecture Foundation
- University of Illinois Chicago
- Maggie Daley Park
- Zhou B Art Center
- Millennium Park
- Chicago Cultural Center
- Chicago Museum Campus Vacations
- Crown Fountain
- South Loop Vacations
- 333 West Wacker Drive
- Art Institute of Chicago
- Merchandise Mart
- Shops at North Bridge
- Cadillac Palace Theatre
- Magnificent Mile Vacations
- Illinois Institute of Technology
- 900 North Michigan Shops
- Muddy Waters’ House
- Wrigley Building
- Rookery
- Auditorium Building and Theatre
- Montrose Beach
- Wrigley Field
- Marshall Field Building
- Film Row Cinema
- Tribune Tower
- 311 S Wacker Dr
- South Commons Vacations
- Skydeck Ledge
- Garfield Park Conservatory
- Symphony Center
- University of Chicago
- Lakefront Trail
- Richard J. Daley Center
- Harold Washington Library Center
- Bridgeport Art Center
- Robert W Roloson Houses
- Carbide and Carbon Building
- The Salt Shed
- Cibc Theatre
- Ping Tom Memorial Park
- Burnham Park
- Maxwell Street Market
- Marina City
- Willis Tower
- Oak Street Beach
- Gen. John Logan Memorial
- Chase Tower
- Driehaus Museum
- Chicago City Hall
- Fisher Building
- North Avenue Beach
- Picasso Statue
- Sr Crown Hall
- Grant Park
- Navy Pier
- Michigan Avenue Bridge
- Holy Name Cathedral
- Ida B Wells House
- Chicago Place Mall
- Anna and Frederick Douglass Park
- Pontiac Building
- Downtown Chicago Vacations
- Griffin Museum of Science and Industry
- Civic Opera House
- Unity Temple
- Water Tower Place
- Cna Center
- Hyde Park Vacations
- Chicago Board of Trade Building
- Roosevelt University
- Depaul University-Loop Campus
- Monadnock Building
- Columbia College Chicago
- American Police Center & Museum
- Michigan Avenue
- Old Colony Building
- Robie House
- Canalport Riverwalk Park
- Lincoln Park Zoo
- Chicago Children's Museum
- Chinatown Vacations
- The Loop Vacations
- Chicago Riverwalk
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.