Englewood Vacations from $602
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The Latest Englewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hotel Felix River North/Magnificent Mile
Aug 20 - Aug 24Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.2/10 - Very Good (2,848 reviews)"Nice staff, easy check-in, and about an 8 minute walk to red line which can get you all over town. No complaints about our stay."Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Sep 30 - Oct 5Level Chicago – Old Town + Flight
Downtown Chicago5 nights4.0 star property9.0/10 - Wonderful (502 reviews)"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."Reviewed July 14, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Saint Clair- Magnificent Mile
Aug 26 - Aug 30Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.4/10 - Very Good (2,041 reviews)"Clean room but the bathroom is the smallest one I've experienced in a hotel."Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Aug 20 - Aug 24Hotel Riu Plaza Chicago + Flight
Downtown Chicago4 nights4.0 star property9.4/10 - Exceptional (4,749 reviews)"The room and hotel exceeded my expectations. The hotel was located in the best spot. I would definitely stay here again."Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago Fulton Market
Aug 20 - Aug 24Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (528 reviews)"Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!"Reviewed July 17, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop
Englewood Hotel Deals
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, (2,599 reviews)
9.4/10
Exceptional
(2,599 reviews)
$264 nightly
The price is $314
$314 total
Aug 17 - Aug 18
Total with taxes and fees
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago Riverwalk4.0 star property
Streeterville, 7.8 mi from Englewood
8.6 out of 10, Excellent, (1,719 reviews)
8.6/10
Excellent
(1,719 reviews)
"The restaurant where they serve breakfast was filthy. We were ere seated at a dirty table with food and some kind of sticky liquid on the seat and food under the table.
The hostess took us to another table and it was dirty as well."
$299 nightly
The price is $355
$355 total
Aug 9 - Aug 10
Total with taxes and fees
9.0 out of 10, Wonderful, (3,498 reviews)
9.0/10
Wonderful
(3,498 reviews)
"Close downtown"
$253 nightly
The price is $301
$301 total
Aug 9 - Aug 10
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile4.0 star property
Streeterville, 8.1 mi from Englewood
8.8 out of 10, Excellent, (2,533 reviews)
8.8/10
Excellent
(2,533 reviews)
$225 nightly
The price is $267
$267 total
Aug 10 - Aug 11
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile4.0 star property
Streeterville, 8 mi from Englewood
8.2 out of 10, Very Good, (2,916 reviews)
8.2/10
Very Good
(2,916 reviews)
$237 nightly
The price is $282
$282 total
Aug 9 - Aug 10
Total with taxes and fees
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park4.5 star property
The Loop, 7.6 mi from Englewood
8.8 out of 10, Excellent, (2,263 reviews)
8.8/10
Excellent
(2,263 reviews)
"Super helpful and friendly staff. Didn’t care for the soap and shampoo smelled like roses and gave me a headache. I wish I knew ahead of time the credits we would receive using certain amenities. I would definitely stay here again. Perfect location."
$349 nightly
The price is $415
$415 total
Aug 9 - Aug 10
Total with taxes and fees
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag Mile3.0 star property
Streeterville, 8.1 mi from Englewood
8.6 out of 10, Excellent, (3,309 reviews)
8.6/10
Excellent
(3,309 reviews)
"Great property to stay while on Chi
Very clean and staff was helpful. I would definitely stay again"
$187 nightly
The price is $222
$222 total
Aug 9 - Aug 10
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.
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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.