Roseland Vacations from $475
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The Latest Roseland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hotel Saint Clair- Magnificent Mile
Sep 24 - Sep 27Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.4/10 - Very Good (2,075 reviews)"Fine stay, good location and good if you want to walk around to some of the key spots around town. Almost good value for money - price was maybe 10-20% more than what we’d like to have paid but decent hotel. Did the job for us!"Reviewed August 1, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Holiday Inn Chicago O'Hare – Rosemont by IHG
Oct 2 - Oct 6Holiday Inn Chicago O'Hare – Rosemont by IHG + Flight
Rosemont4 nights3.0 star property9.0/10 - Wonderful (3,081 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Oct 6 - Oct 9Level Chicago – Old Town + Flight
Downtown Chicago3 nights4.0 star property9.0/10 - Wonderful (512 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Sep 24 - Sep 27Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,883 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Oct 21 - Oct 25Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights4.0 star property9.4/10 - Exceptional (2,626 reviews)"Parking was way too expensive and hard to understand"Reviewed July 31, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop
Discover the most popular places to visit in Roseland
Roseland Hotel Deals
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton4.0 star property
Streeterville, 12.8 mi from Roseland
9.4 out of 10, Exceptional, (2,626 reviews)
9.4/10
Exceptional
(2,626 reviews)
"Parking was way too expensive and hard to understand"
$230 nightly
The price is $273
$273 total
Aug 31 - Sep 1
Total with taxes and fees
7.8 out of 10, Good, (3,247 reviews)
7.8/10
Good
(3,247 reviews)
"If u looking for a place for just sleep this is the one
The location it’s PERFECT! theres not to much to do in the hotel, the rooms are small but it was enough for me and other 3 people in the cuádruple room, we would like it to have a mini fridge or water or coffee at least."
$118 nightly
The price is $140
$140 total
Aug 31 - Sep 1
Total with taxes and fees
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop3.0 star property
The Loop, 11.2 mi from Roseland
8.8 out of 10, Excellent, (2,107 reviews)
8.8/10
Excellent
(2,107 reviews)
$161 nightly
The price is $191
$191 total
Aug 31 - Sep 1
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, 11.2 mi from Roseland
8.8 out of 10, Excellent, (2,398 reviews)
8.8/10
Excellent
(2,398 reviews)
$169 nightly
The price is $201
$201 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, 11.2 mi from Roseland
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
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel4.0 star property
The Loop, 11.6 mi from Roseland
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
8.0 out of 10, Very Good, (10,172 reviews)
8.0/10
Very Good
(10,172 reviews)
$145 nightly
The price is $172
$172 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.