Englewood Vacations from $474
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Englewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hotel Felix River North/Magnificent Mile
Oct 4 - Oct 7Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 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 - ORD • 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 - Level Chicago Fulton Market
Aug 21 - Aug 25Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (530 reviews)"Pictures are misleading. Our “suite” had only modest separation between the bed and sofa bed. The description should have been a studio or junior suite."Reviewed July 19, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Oct 4 - Oct 7Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,753 reviews)"The property was really cool. Staff was amazing and even better breakfast. Best stay ever."Reviewed July 19, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago - River North
Sep 3 - Sep 7Level Chicago - River North + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (1,037 reviews)"Amazing place"Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop MDW - 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, (2,600 reviews)
9.4/10
Exceptional
(2,600 reviews)
$265 nightly
The price is $315
$315 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, (1,721 reviews)
8.6/10
Excellent
(1,721 reviews)
"Absolutely loved the service that I received while staying here. The staff was absolutely lovely. Having multiple options to eat in house is definitely a plus. It’s a huge property with great views. I will be staying here again."
$299 nightly
The price is $355
$355 total
Aug 9 - Aug 10
Total with taxes and fees
9.0 out of 10, Wonderful, (3,500 reviews)
9.0/10
Wonderful
(3,500 reviews)
"Very clean… great location"
$245 nightly
The price is $291
$291 total
Aug 16 - Aug 17
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, (2,535 reviews)
8.8/10
Excellent
(2,535 reviews)
$229 nightly
The price is $272
$272 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, (2,264 reviews)
8.8/10
Excellent
(2,264 reviews)
$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, (3,311 reviews)
8.6/10
Excellent
(3,311 reviews)
$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.