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

Find Romantic Hotels in Hillside, IL from CA $515

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

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

Our top choices for Hillside romantic hotels

1. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
Downtown Evanston
United States
Brian W.
CA $256
CA $515 total
includes taxes & fees
Sep 22 - Sep 23
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
View all properties

Top Hillside Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Really great stay and experience"
Whitney 2-night trip
Posted 1 hour ago
Hyatt Regency Chicago
River Hotel

River Hotel

10/10 Excellent
"The help of staff"
Kavitra 2-night trip
Posted 1 hour ago
River Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"Did have a messed up air conditioner when we first got there. They fixed it immediately and we got it replaced. Other than that good stay."
Jade Gizelle 5-night trip
Posted 1 hour ago
Travelodge by Wyndham Downtown Chicago
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Overall this was a great hotel. The room was clean and all staff were friendly. My only complaints were how much light was still allowed into the room even with the curtains closed and since it's an older building sound carried quite a bit more from room to room than I was expecting."
Bryan 4-night trip
Posted 1 hour ago
Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"I enjoyed my stay. Nice hotel and nice staff"
Whitney 2-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Habitación limpia y un excelente servicio"
Erika 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
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 2 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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 15 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 17 hours ago
InterContinental Chicago Magnificent Mile by IHG

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.

Explore a world of travel with Expedia