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Check availability on Winnetka Romantic Hotels

Tonight
Sep 18 - Sep 19
Tomorrow
Sep 19 - Sep 20
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Top Winnetka Hotel Reviews

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good
"There were a couple of things about this hotel that threw me for a loop (no in room coffee machine -- but plenty of coffee at the bar with choice of skim, half and half and cream; you first encounter the bar versus the registration area), but I would definitely stay here again, and for that I compliment the staff. Fatima greeted us at check in and immediately noticed my daughter had mobility issues and offered to change our room for an accessible one. Since this was my first overnight trip with my daughter I hadn't even thought of that! I appreciated that she saw a way to make our stay better and made it happen. Fatima also always had a smile on her face when we saw her and was always ready to answer any question. I didn't get the name of the doorman we interacted with the most (but I did get a photo with him!), which I regret. He was an older many who worked day shift and he touched my heart when he stayed by my daughter while I went to get our car from the parking garage. He didn't have to do that. The people definitely made this staff wonderful!"
Mary Louise 1-night trip
Posted less than an hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"The hotel was pretty outdated and there was a really bad smell in the bathroom the whole time. The beds were clean though and the staff was helpful. Needs some improvement but was okay for 2 nights! The location is great though!!!"
Kaytlin 2-night trip
Posted less than an hour ago
Travelodge by Wyndham Downtown Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"The room was amazing, I booked a king room and got upgraded to a king suite, it was stunning! The views, the room, the service… 100/10!"
Nia 1-night trip
Posted 12 hours ago
Eurostars Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"The hotel staff are incredibly helpful. The room is updated and very clean. The room fees are higher here than most hotels though."
Mary Grace 2-night trip
Posted 15 hours ago
InterContinental Chicago Magnificent Mile by IHG
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Nice hotel in heart of city"
nIKKI 3-night trip
Posted 15 hours ago
L7 Chicago by LOTTE
River Hotel

River Hotel

8/10 Good
"Great location!"
SEAN 4-night trip
Posted 16 hours ago
River Hotel
The Wade

The Wade

10/10 Excellent
"."
MariaChristina 3-night trip
Posted 20 hours ago
The Wade
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"The staff is fantastic, everyone was kind and helpful. The rooms were clean and met all expectations."
Jonathan 2-night trip
Posted 1 day ago
Hampton Inn Chicago Downtown/Magnificent Mile
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"Elevator situation is not the best but it was a good stay for Lollapalooza"
Christopher 1-night trip
Posted 1 day ago
Hotel Saint Clair- Magnificent Mile

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, Maple Street Beach, or Elder Lane Beach. 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, Maple Street Beach, and Elder Lane Beach 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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