Englewood Vacations from $400
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The Latest Englewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- The Whitehall Hotel, BW Premier Collection
Oct 22 - Oct 25The Whitehall Hotel, BW Premier Collection + Flight
Downtown Chicago3 nights3.5 star property8.4/10 - Very Good (3,939 reviews)"Great location, spacious room. Really comfy bed."Reviewed August 1, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Four Seasons Hotel Chicago
Sep 13 - Sep 19Four Seasons Hotel Chicago + Flight
Downtown Chicago6 nights5.0 star property9.4/10 - Exceptional (1,002 reviews)"I’m from Chicago and I think. It’s the best hotel in the city"Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$4,670$2,476found 1 day agoper traveler - Hotel Riu Plaza Chicago
Oct 22 - Oct 25Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,892 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago - River North
Sep 13 - Sep 19Level Chicago - River North + Flight
Downtown Chicago6 nights4.0 star property9.2/10 - Wonderful (1,042 reviews)"This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities"Reviewed July 30, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago Fulton Market
Sep 2 - Sep 8Level Chicago Fulton Market + Flight
Downtown Chicago6 nights4.0 star property9.2/10 - Wonderful (542 reviews)"Comes with all the comforts of Home."Reviewed July 29, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop
Englewood Hotel Deals
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop3.0 star property
The Loop, 6.4 mi from Englewood
8.8 out of 10, Excellent, (2,109 reviews)
8.8/10
Excellent
(2,109 reviews)
$161 nightly
The price is $191
$191 total
Aug 31 - Sep 1
Total with taxes and fees
Best Western Grant Park Hotel
Best Western Grant Park Hotel2.5 star property
The Loop, 6.4 mi from Englewood
8.2 out of 10, Very Good, (2,753 reviews)
8.2/10
Very Good
(2,753 reviews)
"Very nice location in Grant Park on Michigan Avenue. Staff was friendly overall. Valet attendant was great. (Antoine?). $58 per night valet. We were on 6th floor close to elevator and Ice Machine. I am handicapped so I was happy with location. I brought a cooler to hold my medicines being a diabetic. The ice machine worked the 1st of 3 nights. After that it was broke and my wife had to find limited ice on another floor. It seems that people brought big coolers and were filling them from...
$143 nightly
The price is $170
$170 total
Aug 30 - Aug 31
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago2.0 star property
The Loop, 6.8 mi from Englewood
7.6 out of 10, Good, (2,708 reviews)
7.6/10
Good
(2,708 reviews)
"Everything is clean. The room was always cleaned and ready for us. Just an old building with old smells."
$123 nightly
The price is $147
$147 total
Aug 31 - Sep 1
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton4.0 star property
Streeterville, 8.1 mi from Englewood
9.4 out of 10, Exceptional, (2,630 reviews)
9.4/10
Exceptional
(2,630 reviews)
$230 nightly
The price is $273
$273 total
Aug 31 - Sep 1
Total with taxes and fees
8.0 out of 10, Very Good, (10,180 reviews)
8.0/10
Very Good
(10,180 reviews)
$145 nightly
The price is $172
$172 total
Aug 30 - Aug 31
Total with taxes and fees
9.0 out of 10, Wonderful, (1,007 reviews)
9.0/10
Wonderful
(1,007 reviews)
$158 nightly
The price is $188
$188 total
Aug 30 - Aug 31
Total with taxes and fees
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop3.0 star property
The Loop, 6.4 mi from Englewood
8.8 out of 10, Excellent, (2,403 reviews)
8.8/10
Excellent
(2,403 reviews)
$169 nightly
The price is $201
$201 total
Aug 31 - Sep 1
Total with taxes and fees
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel4.0 star property
The Loop, 6.8 mi from Englewood
9.6 out of 10, Exceptional, (1,293 reviews)
9.6/10
Exceptional
(1,293 reviews)
"Small problem with elevator. It was taken care of quickly"
$167 nightly
The price is $199
$199 total
Aug 30 - Aug 31
Total with taxes and fees
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.
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.