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Valentines in Chicago

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Valentines in Chicago: Recommended rentals

Valentines in Chicago: find your perfect rental from just $61 per night!

House Rosemoor
Feb 12 - Feb 19
House ∙ 4 guests ∙ 2 bedrooms

House with 2 Rooms for 4 Persons

Rosemoor, Chicago, Illinois, United States
$151
per night
Outstanding(1 rating)
$151
per night
View deal
House Fifth City
Feb 12 - Feb 19
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home with BBQ & Yard

Fifth City, Chicago, Illinois, United States
$161
per night
Outstanding(7 ratings)
$161
per night
View deal
Apartment Near North
Feb 12 - Feb 19
Free cancellation
Apartment ∙ 3 guests ∙ 1 bedroom

Child-Friendly Pleasant Rental Apartment | Close to John Hancock Center | Pet-Friendly

Near North, Chicago, Illinois, United States
$175
per night
$175
per night
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Bed and breakfast Bridgeport
Feb 12 - Feb 19
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms

Wonderful B&B with 3 Rooms for 9 Persons

Bridgeport, Chicago, Illinois, United States
$305
per night
Excellent
$305
per night
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Bed and breakfast Wicker Park
Feb 12 - Feb 19
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Beautiful Bed and Breakfast for 6 Persons

Wicker Park, Chicago, Illinois, United States
$228
per night
Outstanding
$228
per night
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Apartment Grand Boulevard
Feb 12 - Feb 19
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment with 2 Rooms for 6 Persons

Grand Boulevard, Chicago, Illinois, United States
$157
per night
(2 ratings)
$157
per night
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Apartment Ukrainian Village
Feb 12 - Feb 19
Free cancellation
Apartment ∙ 10 guests ∙ 4 bedrooms

Family-Friendly Apartment with Grill & Fast Internet

Ukrainian Village, Chicago, Illinois, United States
$220
per night
$220
per night
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Condo Near West Side
Feb 12 - Feb 19
Free cancellation
Condo ∙ 6 guests ∙ 2 bedrooms

Fully Equipped Nice Condo with Garden

Near West Side, Chicago, Illinois, United States
$123
per night
Outstanding(7 ratings)
$123
per night
View deal
Apartment Near North
Feb 12 - Feb 19
Free cancellation
Apartment ∙ 2 guests ∙ 1 bedroom

Children-Friendly Lovely Apartment | Close to John Hancock Center | Pets Are Welcome

Near North, Chicago, Illinois, United States
$128
per night
$128
per night
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Apartment Grand Boulevard
Feb 12 - Feb 19
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-Oriented Pleasant Apartment

Grand Boulevard, Chicago, Illinois, United States
$132
per night
$132
per night
View deal
Apartment Near North
Feb 12 - Feb 19
Free cancellation
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment | Near John Hancock Center

Near North, Chicago, Illinois, United States
$123
per night
$123
per night
View deal
Condo Grand Boulevard
Feb 12 - Feb 19
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with 3 Rooms for 6 Persons

Grand Boulevard, Chicago, Illinois, United States
$380
per night
$380
per night
View deal
Apartment South Austin
Feb 12 - Feb 19
Apartment ∙ 10 guests ∙ 2 bedrooms

Apartment with 2 Rooms for 10 Persons

South Austin, Chicago, Illinois, United States
$272
per night
Outstanding(2 ratings)
$272
per night
View deal
Apartment Jefferson Park
Feb 12 - Feb 19
Free cancellation
Apartment ∙ 4 guests ∙ 1 bedroom

Family-Oriented Holiday Apartment with Barbeque & Yard

Jefferson Park, Chicago, Illinois, United States
$152
per night
Very good(7 ratings)
$152
per night
View deal
Apartment Old Town
Feb 12 - Feb 19
Apartment ∙ 3 guests ∙ 1 bedroom

Children-Friendly Beautiful Holiday Apartment

Old Town, Chicago, Illinois, United States
$185
per night
$185
per night
View deal

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.
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

Apartment Greater Grand Crossing
Feb 12 - Feb 19
$180
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental Apartment with 3 Rooms for 6 Persons

Greater Grand Crossing, Chicago, Illinois, United States
Free cancellation
View deal
Apartment Chatham
Feb 12 - Feb 19
$445
per night
Apartment ∙ 10 guests ∙ 4 bedrooms

Holiday Apartment with 4 Rooms for 10 Persons

Chatham, Chicago, Illinois, United States
Free cancellation
View deal
Apartment Heart of Chicago
Feb 12 - Feb 19
$171
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment with 2 Rooms for 6 Persons

Heart of Chicago, Chicago, Illinois, United States
Free cancellation
View deal

Information about Valentines in Chicago

📏 Average home size 90 m²
😎 Least busy month June
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months 17 °F in January and February
🌧️ Rainiest months March and April

Valentines in Chicago: frequently asked questions

Valentines in Chicago: What is the cost per night?

HomeToGo has incredible vacation rentals, with rates as low as $61 per night.

Valentines in Chicago: does HomeToGo offer a wide variety of vacation rentals for groups of guests?

Apartment rentals in Chicago should be considered for medium-sized groups and families, since they fit 5 people.

Valentines in Chicago: what kinds of vacation rentals are available in Chicago?

Sure, there are 632 House rentals and 2,298 Apartment rentals available in Chicago.

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

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