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Romantic Getaways in Chicago

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

Make Memories on Romantic Getaways in Chicago

The city of Chicago, set on the shores of Lake Michigan, is full of possibilities for sweethearts. With diverse attractions, live jazz, and delicious cuisine, this epic destination has everything for a couple in love. Its wide range of romantic spots sets the mood just right.

Romantic Getaway in Chicago: Top Accommodations

Aparthotel Near North
Jan 13 - Jan 20
-35%
$430
$279 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Aparthotel in Near North with Grill & Pool, Close to John Hancock Center
5.0
"Excellent" (185 ratings)
Near North, Chicago, Illinois, United States
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Aparthotel Near North
Apr 22 - Apr 29
-31%
$1,068
$735 per night
Aparthotel ∙ 8 guests ∙ 3 bedrooms
Aparthotel in Near North with Grill, Pool & Sauna, Near John Hancock Center
4.9
"Excellent" (142 ratings)
Near North, Chicago, Illinois, United States
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Apartment Near North
Dec 16 - Dec 23
$364 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Charming Apartment in Near North, Next to Magnificent Mile
4.9
"Excellent" (82 ratings)
Near North, Chicago, Illinois, United States
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Romantic Places to Visit in Chicago

Romantic Places to Visit in Chicago

For romance, look no further than Chicago. With a multitude of places offering intimate experiences, the city boasts a wide choice of great spots to see with your significant other. Rekindle your love or make sparks fly at these hotspots in Chicago.

  • 1. Buckingham Fountain

    The evening light and music show amid Georgian pink marble and Art Deco-style seahorses makes for perfect relaxation with your partner. The 133 jets spout water every 20 minutes on the hour.

  • 2. Promontory Point

    This humanmade peninsula on Lake Michigan is an ideal point to propose to your lover. Access it via the Lakefront Trail and marvel at the spectacular views of the Chicago skyline. You may mistake the field house at the park for a small castle!

  • 3. Garfield Park Conservatory

    There’s no better place for relaxation for nature-loving couples than at Garfield Park Conservatory. It's a special treat in winter, when the area is coated in snow. Stroll through the conservatory hand-in-hand with your loved one and spot the variety of flora.

  • 4. Adler Planetarium

    Head to the Museum Campus peninsula for an engagement photo session at Adler Planetarium, its outermost point. This historic landmark boasts remarkable views in the city and an eclectic wine menu.

  • 5. The Garden of the Phoenix in Jackson Park

    Stroll through this Japanese garden on Wooded Island and enjoy its permanent art installation with your loved one. Visit in spring and marvel at the blossoming cherry trees.

Best Places to Stay for Romantic Getaway in Chicago

Apartment Roscoe Village
Jul 28 - Aug 4
$182 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Rental Apartment in Roscoe Village with Grill & Yard
5.0
"Excellent" (152 ratings)
Roscoe Village, Chicago, Illinois, United States
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House Hollywood Park
Dec 16 - Dec 23
$262 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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Apartment University Village / Little Italy
Feb 17 - Feb 24
-49%
$555
$280 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Apartment in University Village / Little Italy
5.0
"Excellent" (223 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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Romantic Restaurants in Chicago

Romantic Restaurants in Chicago

Whether it's a lengthy wine list or candlelit table you're seeking, Chicago's romantic restaurants will live up to your expectations and set the perfect mood for a night out. Experience Chicago’s culinary delights at the following eateries.

  • 1. Geja’s Café

    The atmosphere at this candlelit restaurant on 340 West Armitage Avenue is perfect for you and your significant other. The sound of classical and Flamenco guitar welcomes you to try its main dishes and treats such as its famous chocolate fondue.

  • 2. Alinea

    Along 1723 North Halsted Street lies a romantic dining experience at Alinea, whose unique, modern cuisine promises to thrill. The menu changes seasonally, so you and your loved one can savor something new together.

  • 3. Sapori Trattoria

    A gem at Lincoln Park, it serves the best of Italian food. Wash down your favorite pasta with a glass of wine. Sharing a sweet tiramisu with your partner at this serene locale spices up your romantic holiday.

  • 4. Boka

    This intimate eatery offers an extensive wine list, creative cocktails, and specially prepared American favorites such as chicken wings and scallops. The vibrant green wall and the dizzying red-and-white-tile floor gives it an alluring setting ideal for an evening date. Don’t leave before trying the dessert.

  • 5. North Pond

    For locally sourced food amid fantastic views, North Pond ranks among the top choices in Chicago. Pop in for a soft-boiled farm egg served with potato puree, smoked trout, or onion soup.

Recommended Accommodations for Romantic Getaway in Chicago

House West Loop
Aug 18 - Aug 25
$257 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in West Loop with Private Balcony
4.8
"Excellent" (36 ratings)
West Loop, Chicago, Illinois, United States
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Apartment North Center
Dec 9 - Dec 16
-48%
$239
$124 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Family Friendly Apartment in North Center
5.0
"Excellent" (101 ratings)
North Center, Chicago, Illinois, United States
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Apartment Near North
Jan 6 - Jan 13
-51%
$392
$191 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Apartment in Near North with On-Site Parking, Near John Hancock Center
4.9
"Excellent" (22 ratings)
Near North, Chicago, Illinois, United States
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What to Pack for Your Romantic Getaway in Chicago

What to Pack for Your Romantic Getaway in Chicago

Romantic getaways are for spending quality time with your loved one. Leave more time for yourselves by planning ahead. Here's what you should pack.

  • 1. Appropriate clothes

    Pack a few pairs of jeans/pants alongside pull-on/button-up shirts. Depending on the season, a coat or raincoat could be useful, as would a swimsuit.

  • 2. Shoes

    You may be covering a lot of ground on your sightseeing adventures, so bring comfortable walking shoes to avoid blisters. Flat shoes come in handy if you're heading out for a night of dancing. For hiking, bring sturdy boots.

  • 3. Tech

    Bring a phone charger to keep in touch with your friends and family, and headphones if you'd like to listen to music or an audiobook. Have your camera with you to document the lasting memories.

  • 4. Other essentials

    Carry an ATM card and some small bills in case your eatery accepts cash-only payment. Make copies of important documents such as passports, and keep the originals and duplicates separately. Bringing your medical insurance card is also a good idea.

Top Offers for Romantic Getaway in Chicago

Apartment Roscoe Village
Jul 28 - Aug 4
$182 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Rental Apartment in Roscoe Village with Grill & Yard
5.0
"Excellent" (152 ratings)
Roscoe Village, Chicago, Illinois, United States
Details
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House Hollywood Park
Dec 16 - Dec 23
$262 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
Details
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Apartment University Village / Little Italy
Feb 17 - Feb 24
-49%
$555
$280 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Apartment in University Village / Little Italy
5.0
"Excellent" (223 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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Frequently Asked Questions

Romantic Getaways in Chicago: What is the vacation rental cost in Chicago?

You can get an incredible rental from $209 and find discounts up to 63%!

Can I find a vacation home for a group for Romantic Getaways in Chicago?

The average size for a Apartment rental is 81 m² and can fit 4 guests on average which is ideal for medium-sized groups and families.

Do many one-bedroom vacation homes are available for a short stay in Chicago?

You can find more than 9,097 accommodations for rent in Chicago with prices starting at $69 per night.

Can you book rentals in Chicago offer a pool?

Of course, over 28% of couples accommodations in Chicago come with a pool.

Are there cheap romantic retreats in Chicago?

Couples vacation rental prices in Chicago start at just $69 and can go up to $473 per night.

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

There are many House rental and Apartment rental that are great for Romantic Getaways in Chicago.

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

Romantic Getaways in Chicago Inspiration

Top Vacation Ideas in Chicago

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