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Romantic Getaways in Chicago

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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

House Grand Boulevard
Aug 16 - Aug 23
$200 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Grand Boulevard

5.0
Outstanding (7 ratings)
Grand Boulevard, Chicago, Illinois, United States
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House West Town
Apr 20 - Apr 27
$252 per night
House ∙ 10 guests ∙ 3 bedrooms

House in West Town with Grill & Patio, Queen Sofabed

4.8
Outstanding (49 ratings)
West Town, Chicago, Illinois, United States
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Apartment West Town
Apr 19 - Apr 26
$160 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Lovely Apartment in West Town with Private Terrace + Magnificent Views

4.9
Outstanding (30 ratings)
West Town, 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

House Uptown
Apr 11 - Apr 18
$1,141 per night
House ∙ 21 guests ∙ 6 bedrooms

Vacation Home in Uptown with Yard, Patio & Grill

5.0
Outstanding (146 ratings)
Uptown, Chicago, Illinois, United States
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House Humboldt Park
May 11 - May 18
$57 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Humboldt Park with Patio

4.1
Very good (13 ratings)
Humboldt Park, Chicago, Illinois, United States
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Condo Lake View
Apr 11 - Apr 18
-31%
$418
$288 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Lake View with Patio & Grill

Lake View, 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 Beverly
Aug 16 - Aug 23
$257 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Beverly with Grill & Patio

3.3
(21 ratings)
Beverly, Chicago, Illinois, United States
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Condo West Town
Apr 11 - Apr 18
$297 per night
Condo ∙ 9 guests ∙ 2 bedrooms

Condo in West Town with Private Terrace + Skyline View

5.0
Outstanding (206 ratings)
West Town, Chicago, Illinois, United States
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House Near North Side
Apr 22 - Apr 29
-65%
$285
$100 per night
House ∙ 10 guests ∙ 2 bedrooms

Nice House in Near North Side

5.0
Outstanding (2 ratings)
Near North Side, 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 Ukrainian Village
Jul 6 - Jul 13
$753 per night
Apartment ∙ 10 guests ∙ 4 bedrooms

Apartment in Ukrainian Village with Private Balcony + Great View

5.0
Outstanding (34 ratings)
Ukrainian Village, Chicago, Illinois, United States
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Apartment Park Manor
Jul 6 - Jul 13
$138 per night
Apartment ∙ 8 guests ∙ 4 bedrooms

Rental Apartment in Park Manor with Yard & Patio

4.9
Outstanding (7 ratings)
Park Manor, Chicago, Illinois, United States
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Condo Rogers Park
Apr 12 - Apr 19
$171 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Rogers Park with Rear Garden

4.9
Outstanding (222 ratings)
Rogers Park, Chicago, Illinois, United States
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Information about Romantic Getaways in Chicago

💳 Highest rates in October
😎 Least busy month May
🛏️ Popular home types House rental and Apartment rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months 17 °F in January and February
🌧️ Rainiest months March and April

Frequently Asked Questions

Romantic Getaways in Chicago: What is the nightly cost of a stay?

HomeToGo offers great rentals for Romantic Getaways in Chicago, with retes as low as $50 per night.

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

in Chicago, medium-sized groups and families should consider Apartment rental since they can fit 4 people.

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

There are more than 9,818 romantic getaways for rent in Chicago with nightly prices starting from $50 per night.

What kinds of vacation rentals are available for Romantic Getaways in Chicago?

You can browse 2,022 Apartment rental and 509 House rental for Romantic Getaways in Chicago right here on HomeToGo.

Are there affordable romantic getaways in Chicago?

Couples home rental prices in Chicago start at just $50 and can go up to $661 per night.

Can you find vacation rentals in Chicago include a pool?

Yes, more than 24% of couples accommodations in Chicago offer a pool.

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