Find Romantic Hotels in Oakland, Chicago from $88

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Check availability on Oakland Romantic Hotels

Our top choices for Oakland romantic hotels

Lobby
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2961)
"Great location and great staff!!"
United States
lynne
$79 nightly
The price is $93
Jan 14 - Jan 15, 2026
Total with taxes and fees
Aloft Chicago Mag Mile
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2742)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
$103 nightly
The price is $120
Jan 11 - Jan 12, 2026
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3011)
"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
View from room
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3483)
"Great place to stay "
United States
RaShawna
$81 nightly
The price is $95
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3152)
"Amazing stay very clean and beautiful views "
United States
Deigo
$94 nightly
The price is $110
Jan 13 - Jan 14, 2026
Total with taxes and fees
Eurostars Magnificent Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2260)
"This place was amazing !"
United States
Jayla Danyell
$122 nightly
The price is $143
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
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
Ballroom
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3144)
"The location, hotel, and views are absolutely fantastic!"
United States
Frederick
$141 nightly
The price is $166
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Royal Sonesta Chicago Downtown
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, (1786)
"Great stay in a great area."
United States
Giselle
$75 nightly
The price is $88
Dec 17 - Dec 18
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 8 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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