Englewood Vacations
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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.
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- The Talbott, Autograph Collection
Jul 1 - Jul 4The Talbott, Autograph Collection + Flight
Downtown Chicago3 nights9.4/10 - Exceptional (116 reviews)"We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "Reviewed May 17, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago Fulton Market
Aug 10 - Aug 15Level Chicago Fulton Market + Flight
Downtown Chicago5 nights9.2/10 - Wonderful (488 reviews)"Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."Reviewed May 22, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Aug 10 - Aug 15Level Chicago – Old Town + Flight
Downtown Chicago5 nights9.0/10 - Wonderful (480 reviews)"Super nice"Reviewed May 20, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - Viceroy Chicago
Jul 31 - Aug 4Viceroy Chicago + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (1,231 reviews)"We had an incredible stay here. The room was very nice as we stayed in a junior suite so the extra charge was definitely worth it. You’re on the 17th floor and you’re able to have a good view of the city. You also are one floor away from the rooftop restaurant and bar. The decor and aesthetics in the hotel are top-notch. Definitely picture worthy. Definitely walkable and it’s less than quarter mile from the hotel to the lake. 10 out of 10 definitely recommend."Reviewed May 23, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Kimpton Gray Hotel by IHG
Jul 31 - Aug 4Kimpton Gray Hotel by IHG + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (1,003 reviews)"Great hotel. Loved the lobby and our room. Would definitely stay here again."Reviewed May 19, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,134 reviews)
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."
Reviewed on May 23, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $185 total per night from May 25 to May 26
$185 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (4,221 reviews)
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."
Reviewed on May 24, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
$123 nightly
The price is $146 total per night from May 25 to May 26
$146 total
May 25 - May 26
Total with taxes and fees
7.8/10 Good! (1,464 reviews)
"There're bed bugs. Be careful"
Reviewed on May 24, 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.
Discover the most popular places to visit in Englewood
Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(4,925 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
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- Chicago Vacations
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- Greater Salem Baptist Church
- Visit South Englewood
- Visit Washington Park
- Visit West Englewood
- Dusable Museum of African-American History
- Griffin 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 Washington Park Court
- 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.