Englewood Vacations from $595
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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
Level Chicago – Old Town
Reviewed on Aug 15, 2026
Swissotel - Chicago
Reviewed on Aug 16, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Aug 16, 2026
Four Seasons Hotel Chicago
Reviewed on Aug 16, 2026
Where to stay in Englewood
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Englewood Hotel Deals
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast
"The hotel didn’t necessarily look like what the pictures showed. Although the hotel was nice enough and in a quiet section of the neighborhood, I feel like the lobby needed a little more light. The room I stayed in was very basic and i didn’t like that I could hear the toilet above me flush very ..."
Reviewed on Aug 16, 2026
Hilton Chicago O'Hare Airport
"So convenient for a late-night flight in and early-morning departure. We like the workout facility also. And it is very quiet"
Reviewed on Aug 16, 2026
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
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
- Ohio Street Beach
- 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