Find Romantic Hotels in Winnetka, IL

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Check availability on Winnetka Romantic Hotels

Our top choices for Winnetka romantic hotels

Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,078 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is NT$2,684
NT$3,151 total
includes taxes & fees
Feb 22 - Feb 23
Aloft Chicago Mag Mile
Rooftop bar, alfresco dining, open daily

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,039 reviews)
"Clean rooms, great staff, and great location."
United States
Romel
The price is NT$2,811
NT$4,041 total
includes taxes & fees
Feb 22 - Feb 23
The Godfrey Hotel Chicago
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,042 reviews)
"Great place"
United States
Omar
The price is NT$2,013
NT$3,290 total
includes taxes & fees
Feb 24 - Feb 25
Warwick Allerton - Chicago
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,287 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is NT$4,247
NT$5,775 total
includes taxes & fees
Feb 21 - Feb 22
Palmer House a Hilton Hotel
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (1,292 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is NT$3,266
NT$3,834 total
includes taxes & fees
Feb 16 - Feb 17
The Chicago Hotel Collection Ambassador Gold Coast
Meeting facility

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,004 reviews)
"Very clean, quiet, and warm reception and service from the staff. "
United States
tim
The price is NT$2,534
NT$3,719 total
includes taxes & fees
Feb 12 - Feb 13
Millennium Knickerbocker Chicago
Ice skating

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,241 reviews)
"Amazing hotel and staff!"
United States
Corey
Silversmith Hotel Chicago Downtown
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,229 reviews)
"Nice location, friendly staff and room was nice"
United States
DeAshley
The price is NT$3,032
NT$3,559 total
includes taxes & fees
Feb 22 - Feb 23
Eurostars Magnificent Mile
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (9,873 reviews)
"Clean room, centrally located hotel. Food menu at bar a bit limited but loads of places around to eat at. Great stay"
United Kingdom
Jeff
The price is NT$2,827
NT$3,319 total
includes taxes & fees
Feb 11 - Feb 12
Congress Plaza Hotel
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1,200 reviews)
"Clean, great customer service, "
United States
Arturo
The Chicago Hotel Collection - 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 Winnetka Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Very clean room has everything you need. Hotel is walking distance from all the main attractions. "
Arturo 1-night trip
Posted 5 hours ago
Hyatt Regency Chicago

Frequently asked questions

Searching for romantic hotels in Winnetka?
Are you looking for a romantic escape? You might consider checking out some of the nearby sights and attractions such as Lake Michigan, Elder Lane Beach, or Chocolate Box. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Winnetka?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Winnetka: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Winnetka is 48 inches.
What is there to do in Winnetka?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all that Winnetka has to offer. Lake Michigan, Elder Lane Beach, and Chocolate Box are worth a stop when you're out and about.
What's the best way to get to Winnetka and around town during my romantic getaway?
This information about transportation options in Winnetka might help your romantic trip go off without a hitch: If you're looking to fly to Winnetka, the closest major airport is Chicago, IL (PWK-Chicago Executive), located 8.4 mi (13.5 km) from the city center. To explore the surrounding area, ride one of the trains from Winnetka Station or Winnetka Indian Hill Station.

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