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Valentines in Chicago

Chicago
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Planning an Unforgettable Valentine's Day in Chicago

Bold architecture, iconic skyscrapers, a dazzling skyline, and stunning sights such as those along the Lakefront trail are just some of the treats for an unforgettable Valentines in Chicago. From red roses to thoughtful cards and an eclectic jazz music scene with scrumptious meals and drinks, this populous city in Illinois is one of the best places to celebrate your love.

Valentines Day Travel in Chicago: Top Accommodations

Apartment Roscoe Village
Feb 12 - Feb 19
$182 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Rental Apartment in Roscoe Village with Grill & Yard
5.0
"Excellent" (153 ratings)
Roscoe Village, Chicago, Illinois, United States
Details
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House Hollywood Park
Feb 12 - Feb 19
$261 per night
House ∙ 5 guests ∙ 2 bedrooms
Entire House in Hollywood Park with Free Parking
5.0
"Excellent" (10 ratings)
Hollywood Park, Chicago, Illinois, United States
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Aparthotel Near North
Feb 12 - Feb 19
$1,053 per night
Aparthotel ∙ 8 guests ∙ 3 bedrooms
Aparthotel in Near North with Grill, Pool & Sauna, Near John Hancock Center
4.9
"Excellent" (144 ratings)
Near North, Chicago, Illinois, United States
Details
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Best Things To Do on Valentines Day in Chicago

Best Things To Do on Valentines Day in Chicago

Valentines in Chicago is one of the city's most romantic days. With streets and malls decked out in different shades of red and flowers everywhere, Chicago makes it possible for you to celebrate love in style, pomp, and color. The city offers a plethora of activities to help celebrate this special day, including romantic strolls along Lake Michigan and a Valentine's Day cruise.

  • 1. Romantic dinner at Geja's Café

    Whisk your lover away for a romantic dinner at Geja's Café. This intimate restaurant continues to be one of Chicago's most romantic, a reputation it has maintained for the past 50 years. With candlelit dinners and classical background music, Geja's Café offers the perfect ambiance to kindle romance. Enjoy a three-course dinner with a delicious fondue appetizer, a wide array of main course dinner selections including sea scallops and Gulf shrimp, and delectable desserts with the perfect wine pairing. Be sure to make reservations in advance.

  • 2. Indulge in sightseeing on a Valentine's cruise

    This lakefront cruise provides the perfect opportunity to take your romance game up a notch. Enjoy a scenic ride as you dine on tasty gourmet food with delicious wine pairings. Dance the night away to smooth DJ tunes and live music. Enjoy the refreshing evening breeze in the arms of your partner on the upper deck, drink in hand, as you make unforgettable memories with the city's magical skyline bearing witness to your special day.

  • 3. Magical spin on the iconic Centennial Wheel

    Soaring to a dizzying height of almost 200ft, the Centennial Wheel at Chicago's historic Navy Pier is the best way to end your romantic night. Enjoy panoramic views of the city, including marveling at the Tribune and Willis Towers, which stand among the rest of the city's impressive skyline. Sweep your partner off their feet with breathtaking views of enchanting Lake Michigan as you share a private moment and whisper words of love in the privacy of your gondola.

  • 4. Stop at the Chicago Botanic Garden Orchid Show

    Valentine's Day is never complete without flowers. The Chicago Botanic Garden Orchid Show lets you take in blooms galore as you stroll hand-in-hand and inhale the flower-scented air. See countless flowers, then share delicious handcrafted truffles and chocolates from Vosges Haut-Chocolat, with exotic flavors that will make your mouth water.

Best Places to Stay for Valentines Day Travel in Chicago

House Lake View East
Feb 12 - Feb 19
$380 per night
House ∙ 20 guests ∙ 6 bedrooms
House in Lake View East with Grill & Yard
5.0
"Excellent" (13 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment University Village / Little Italy
Feb 12 - Feb 19
$280 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Apartment in University Village / Little Italy
5.0
"Excellent" (227 ratings)
University Village / Little Italy, Chicago, Illinois, United States
Details
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House Jefferson Park
Feb 12 - Feb 19
$160 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Jefferson Park with Yard
5.0
"Excellent" (36 ratings)
Jefferson Park, Chicago, Illinois, United States
Details
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Frequently Asked Questions

Valentines in Chicago: How much does it cost to rent a vacation rental in Chicago?

The average cost for a vacation home in Chicago is between $206 and $473 per night.

Can I find a vacation rental for a large group for Valentines in Chicago?

Usually the size of a Apartment rental is 81 m² and may fit 4 people on average which is great for medium-sized groups and families.

What types of vacation homes can i book for Valentines in Chicago?

You can choose from 334 House rental and 2,029 Apartment rental for Valentines in Chicago on HomeToGo.

The Weather in Chicago

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Average Nightly Rental Prices in Chicago

Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental Availability Information in Chicago

Valentines in Chicago Inspiration

Top Vacation Ideas in Chicago

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