Find Romantic Hotels in Oakland, Chicago from $91

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Our top choices for Oakland romantic hotels

Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3012)
"Enjoyed this hotel stay. "
United States
Kimberly
$88 nightly
The price is $104
Dec 21 - Dec 22
Total with taxes and fees
Warwick Allerton - Chicago
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3393)
"I always love staying at this place when I visit"
Canada
William
$161 nightly
The price is $189
Dec 28 - Dec 29
Total with taxes and fees
Hyatt Regency Chicago
City view
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2005)
"Great location, clean hotel"
United States
Andre
$109 nightly
The price is $128
Dec 17 - Dec 18
Total with taxes and fees
Millennium Knickerbocker Chicago
Lobby sitting area
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (1787)
"Great stay in a great area."
United States
Giselle
$78 nightly
The price is $91
Dec 18 - Dec 19
Total with taxes and fees
Hotel Saint Clair- Magnificent Mile
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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Top Oakland Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Spacious rooms , free drinks and great breakfast "
Ebony 3-night trip
Posted 16 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Frequently asked questions

Searching for romantic hotels in Oakland?
If you and your partner need some romantic time away, we've got just the thing. If you want to see some of the sights in Oakland, you might make a stop by Lake Michigan or 41st Street Beach. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
What is there to do in Oakland?
There's nothing better than wandering around a new place with your sweetheart, so consider checking out all that Oakland has to offer. You might consider a stop at Lake Michigan or 41st Street Beach while you're out and about.

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