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Valentines in Chicago

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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 The Gap
Feb 15 - Feb 22
$130 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Lovely Rental Apartment in The Gap

4.0
Very good (1 rating)
The Gap, Chicago, Illinois, United States
Free cancellation
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House Near West Side
Feb 15 - Feb 22
$220 per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation Home in Near West Side with Grill

5.0
Outstanding (2 ratings)
Near West Side, Chicago, Illinois, United States
Free cancellation
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Apartment South Austin
Feb 15 - Feb 22
$169 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in South Austin with Yard

5.0
Outstanding (1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
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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 Ravenswood
Feb 15 - Feb 22
$400 per night
House ∙ 8 guests ∙ 4 bedrooms

Wonderful House in Ravenswood with Hot Tub

Ravenswood, Chicago, Illinois, United States
Free cancellation
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Apartment South Austin
Feb 15 - Feb 22
$148 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment in South Austin

5.0
Outstanding (1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
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Apartment Grand Boulevard
Feb 12 - Feb 19
$173 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment in Grand Boulevard

3.0
(2 ratings)
Grand Boulevard, Chicago, Illinois, United States
Free cancellation
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Information about Valentines in Chicago

💳 Highest rates in October
🥳 Busiest month February
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months January and February
🌧️ Rainiest months March and April

Frequently Asked Questions

Valentines in Chicago: What is the cost per night of stay?

The average price for a vacation rental in Chicago is usually around $123 and $724 per night.

Can I find a vacation home for a group of guests for Valentines in Chicago?

Apartment rental in Chicago can fit 4 people.

What kinds of vacation rentals can i book for Valentines in Chicago?

You can find 544 House rental and 2,026 Apartment rental for Valentines in Chicago on HomeToGo.

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Average Nightly Rental Prices in Chicago

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Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental availability information in Chicago

Valentines in Chicago Inspiration

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