A lush green valley with a winding road, steep mountains, and a misty atmosphere.

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Check availability on Hillside 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 Hillside Hotel Reviews

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 3 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 5 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 6 hours ago
L7 Chicago by LOTTE
River Hotel

River Hotel

8/10 Good
"Great location!"
SEAN 4-night trip
Posted 6 hours ago
River Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"It is a bit outdated and needs an upgrade. The place is clean, well maintained however and staff helpful. The room needs more outlets. Outlets are located on the desk and very slow to fully charge phone. Location is great! Everything is in walking distance- Grant and Millennium Parks, Michigan Ave, bus/train easily accessible, State St for shopping, etc. No refrigerator nor microwave in the room."
Morenike 5-night trip
Posted 6 hours ago
Travelodge by Wyndham Downtown Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"great"
Britney 1-night trip
Posted 10 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
The Wade

The Wade

10/10 Excellent
"."
MariaChristina 3-night trip
Posted 11 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 14 hours 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 21 hours ago
Hotel Saint Clair- Magnificent Mile

Frequently asked questions

Searching for romantic hotels in Hillside?
Are you looking for a romantic getaway? Our guests also enjoy Hillside for its restaurants and shopping. If you want to see some sights and attractions in the greater Hillside area, you might head to Wrigley Field, Soldier Field, or Navy Pier. If you'd like to stay close to 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 Hillside?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Hillside: The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Hillside are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Hillside?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all that Hillside has to offer. If you and your partner are interested in sampling the area's cuisine, you'll love Hillside for its array of dining options. There's plenty to see in the greater Chicago area, so you might plan to visit Wrigley Field, Soldier Field, or Navy Pier.
What's the best way to get to Hillside and around town during my romantic getaway?
This information about transportation options in Hillside might help your romantic getaway go off without a hitch: To get to Hillside, you can fly into Chicago O'Hare Intl. Airport (ORD), which is the closest major airport, located 6.9 mi (11 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

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