Best & Cheap Romantic Getaways in Chicago, IL

Compare romantic getaways, From $28/night

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Best & Cheap Romantic Getaways in Chicago, IL: Top Deals

Palmer House a Hilton Hotel
Hotel
Palmer House a Hilton Hotel
4.1 (3712 reviews)
This luxurious Palmer House a Hilton Hotel is located in the heart of Chicago, near popular restaurants such as Xoco and Giordano's Pizza, activities like The Art Institute of Chicago and Shedd Aquarium, and trails like The Lakefront Trail. Pets are also allowed at this hotel.
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$212 /night
The Hotel at Midtown
Resort
The Hotel at Midtown
4.3 (101 reviews)
This Resort is located in Midtown Chicago and offers a convenient location for travelers to explore the city. Popular nearby restaurants include The Purple Pig, RPM Italian, and Pizano's Pizza & Pasta. Guests can also enjoy activities such as taking a stroll along the Lakefront Trail or visiting the Lincoln Park Zoo.
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$209 /night
LEVEL ◆ Three Bedroom Executive Suite + Balcony
Apartment · 8 Guests · 3 Bedrooms
LEVEL ◆ Three Bedroom Executive Suite + Balcony
This luxurious 3 bedroom executive suite is located in the heart of Chicago, close to popular restaurants such as Lou Malnati's Pizzeria, Giordano's, and Taqueria El Asadero. It also offers easy access to activities like kayaking on Lake Michigan, exploring the Lincoln Park Zoo, or hiking along The 606 Trail. With its convenient location and comfortable accommodations for up to 8 people, this Apartment makes an ideal home base for any city getaway.
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$1554 /night*
Spacious Wicker Park 2BR with Patio Deck by Zencity
Apartment
Spacious Wicker Park 2BR with Patio Deck by Zencity
4.8 (4 reviews)
This Apartment is located in Wicker Park, Chicago and offers a spacious two-bedroom with a patio deck. Nearby popular attractions include the 606 Trail, Wicker Park Farmers Market, Big Star restaurant, and the Milwaukee Avenue Arts District.
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$157 /night
ACME Hotel Company
Hotel
ACME Hotel Company
4.4 (611 reviews)
This ACME Hotel Company is a pet friendly hotel located in the heart of Chicago. It is close to popular restaurants such as Lou Malnati's Pizzeria and Giordano's Pizza, attractions like Navy Pier and Millennium Park, and outdoor trails like The 606 Bloomingdale Trail.
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$159.2 /night
Hilton Garden Inn Chicago Downtown South Loop
Hotel
Hilton Garden Inn Chicago Downtown South Loop
4.1 (706 reviews)
This Hotel, Hilton Garden Inn Chicago Downtown South Loop, is located in the heart of downtown Chicago. Popular restaurants nearby include Girl & The Goat, Giordano's Pizzeria and Sushi-San. Popular activities near this hotel include Navy Pier, Lincoln Park Zoo and Millennium Park. There are also plenty of trails available to explore such as The Lakefront Trail and The Bloomingdale Trail. Pets are unfortunately not allowed at this hotel.
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$114 /night
SPRING PRICING SPECIAL! Visit me February-April 2022!!!!
Apartment · 4 Guests · 2 Bedrooms
SPRING PRICING SPECIAL! Visit me February-April 2022!!!!
4.8 (4 reviews)
This Apartment is a great place to stay for those looking to explore the city of Chicago. It is located within walking distance of popular restaurants, such as The Purple Pig, Yolk, and Beatrix, and nearby activities like kayaking on Lake Michigan or visiting the Art Institute of Chicago. There are also trails in the area, such as the North Shore Channel Trail and the Boulevard Lakefront Tour, that provide spectacular views of the city.
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$306 /night*
Four Seasons Hotel Chicago
Hotel
Four Seasons Hotel Chicago
4.6 (227 reviews)
This luxurious Four Seasons Hotel Chicago offers a prime location near popular attractions such as the Magnificent Mile, Navy Pier, and John Hancock Center. There are plenty of restaurants in the area including Gibson's Bar & Steakhouse, RPM Italian, and Wildfire. Guests can also explore nearby trails such as the Lakefront Trail, North Branch Trail, and Forest Preserve Trail or enjoy activities such as kayaking, paddle boarding, and biking. Pets are allowed at this hotel.
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$525 /night
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Condo · 2 Guests · 6 Bedrooms
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
4.9 (53 reviews)
This luxurious duplex penthouse is located in the heart of Chicago, offering an outstanding location. It can sleep up to two people and does not allow pets. Popular nearby restaurants include The Dearborn, Beatrix River North, and RPM Italian. Activities nearby include kayaking along the Chicago River, visiting the Art Institute of Chicago, and exploring the Lincoln Park Zoo. There are also a number of trails around the area, such as the Lakefront Trail and the Bloomingdale Trail.
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$1495 /night*
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Which Price Range Is Considered As A Good Deal in Chicago, IL Area?
Vacation Apartment & House Rental Price Information in Chicago, IL
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The graph shows the percentages of vacation homes in each price bucket. Chicago has the largest percentage (27.59%) of homes in $100 - $150 price range.
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How Many Accommodations Are Pets Allowed in Chicago, IL?
Pets Allowed vs Not Allowed in Chicago, IL
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17.57% of vacation homes in Chicago are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Are you looking for romantic restaurants in Chicago, IL?
Romantic Restaurants in Chicago
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Chicago is the perfect destination for a romantic getaway or honeymoon. With stunning skyline views and delicious cuisine, the city offers plenty of options for couples to enjoy an intimate dinner. Here are some of the best romantic restaurants in Chicago.

  • The Signature Room at the 95th: This restaurant boasts spectacular 360-degree views of Lake Michigan, the John Hancock Building, and the Chicago skyline from its 95th floor location. Enjoy classic American fare with your significant other while taking in the breathtaking sights.
  • Bavette’s Bar & Boeuf: This modern steakhouse serves up classic French dishes in a cozy atmosphere. It features a romantic bar area with dimmed lighting and leather banquettes, making it ideal for an intimate evening out.
  • Acanto Restaurant & Wine Bar: This Italian-inspired restaurant features an outdoor patio and garden that’s perfect for a romantic dinner. The menu includes fresh seafood and handmade pastas, as well as an extensive wine list.
What romantic activities can couples do in Chicago?
Romantic Activities for Couples in Chicago
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From exploring the city's iconic architecture to taking a boat ride on the lake, there are plenty of ways for couples to enjoy each other's company in Chicago. Here are some of the most romantic things to do in the Windy City.

  • Architecture Boat Tour: Take a guided tour down the Chicago River to see the city's famous architectural landmarks. This two-hour cruise also provides stunning views of the skyline and nearby neighborhoods.
  • SkyDeck Chicago: Soar 1,353 feet above the city streets at SkyDeck Chicago. Take in panoramic views of the cityscape and the lakefront with your special someone.
  • Museum of Contemporary Art: Explore the world of modern and contemporary art together at the Museum of Contemporary Art. Stroll through the galleries and take part in interactive installations during your visit.
Where Should We Visit in Chicago, IL Area?
Top Rated Places to Visit in Chicago, IL
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Which Airports Should I Choose To Get To Chicago, IL?
Suggested Airports in Chicago, IL
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