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Romantic Getaways in Chicago

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Romantic Getaways in Chicago: Recommended rentals

Romantic Getaways in Chicago: find your perfect rental from just $80 per night!

House West Loop
Aug 3 - Aug 10
House ∙ 9 guests ∙ 3 bedrooms

Family-friendly vacation home with barbecue | City view | Pets allowed

West Loop, Chicago, Illinois, United States
$388
per night
Excellent(68 ratings)
$388
per night
View deal
Condo Lincoln Park
Mar 18 - Mar 25
Condo ∙ 8 guests ∙ 5 bedrooms

Family-friendly condo with garden & patio

Lincoln Park, Chicago, Illinois, United States
$506
per night
Outstanding(37 ratings)
$506
per night
View deal
Apartment Rush & Division
Apr 1 - Apr 8
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-friendly rental apartment with terrace | Close to John Hancock Center | City view

Rush & Division, Chicago, Illinois, United States
$467
per night
Outstanding(7 ratings)
$467
per night
View deal
Apartment Near North
Mar 18 - Mar 25
Apartment ∙ 7 guests ∙ 2 bedrooms

Holiday apartment with terrace | Near John Hancock Center | City view

Near North, Chicago, Illinois, United States
$142
per night
Good(22 ratings)
$142
per night
View deal
Apartment Heart of Chicago
Jul 5 - Jul 12
Apartment ∙ 8 guests ∙ 2 bedrooms

Holiday apartment with patio, grill & hot tub

Heart of Chicago, Chicago, Illinois, United States
$182
per night
Outstanding(5 ratings)
$182
per night
View deal
Condo East Village
Jul 5 - Jul 12
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with patio & BBQ | Suitable for remote work

East Village, Chicago, Illinois, United States
$634
per night
$634
per night
View deal
Apartment Rush & Division
Jul 6 - Jul 13
Apartment ∙ 10 guests ∙ 4 bedrooms

Family-friendly wonderful apartment with terrace, pool & barbeque | Near John Hancock Center | City view | Beach nearby | Good for workation | Pets are welcome

Rush & Division, Chicago, Illinois, United States
$876
per night
Outstanding(9 ratings)
$876
per night
View deal
Condo Rogers Park
Aug 9 - Aug 16
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped condo with garden, barbeque & jacuzzi | Nature view | Pets are welcome

Rogers Park, Chicago, Illinois, United States
$297
per night
Outstanding(246 ratings)
$297
per night
View deal
Apartment Wicker Park
-41%
Jun 1 - Jun 8
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment | Good for workation

Wicker Park, Chicago, Illinois, United States
$573$420
per night
Excellent(4 ratings)
$573$420
per night
View deal
House Avalon Park
Jun 21 - Jun 28
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly vacation home | Suitable for remote work

Avalon Park, Chicago, Illinois, United States
$469
per night
Outstanding(1 rating)
$469
per night
View deal
House Bronzeville
Sep 13 - Sep 20
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio | Suitable for remote work

Bronzeville, Chicago, Illinois, United States
$583
per night
Outstanding(30 ratings)
$583
per night
View deal
Apartment Streeterville
Mar 18 - Mar 25
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with terrace | Near John Hancock Center | City view | Good for workation

Streeterville, Chicago, Illinois, United States
$309
per night
Excellent(38 ratings)
$309
per night
View deal
Apartment Logan Square
Apr 1 - Apr 8
Apartment ∙ 4 guests ∙ 3 bedrooms

Beautiful apartment | Pets allowed

Logan Square, Chicago, Illinois, United States
$128
per night
Outstanding(8 ratings)
$128
per night
View deal
Apartment South Loop
Apr 13 - Apr 20
Apartment ∙ 16 guests ∙ 2 bedrooms

Rental apartment with 2 rooms for 16 persons

South Loop, Chicago, Illinois, United States
$738
per night
Outstanding(2 ratings)
$738
per night
View deal
Condo Wrigleyville
Aug 8 - Aug 15
Condo ∙ 9 guests ∙ 4 bedrooms

Condo | Pet-friendly

Wrigleyville, Chicago, Illinois, United States
$592
per night
$592
per night
View deal

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 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 South Deering
Jun 28 - Jul 5
$289
per night
House ∙ 8 guests ∙ 4 bedrooms

House with garden | Suitable for remote work

5.0
Outstanding(1 rating)
South Deering, Chicago, Illinois, United States
View deal
Condo Park West
Sep 19 - Sep 26
$597
per night
Condo ∙ 12 guests ∙ 4 bedrooms

Child-friendly spacious condo with garden | Suitable for remote work

5.0
Outstanding(2 ratings)
Park West, Chicago, Illinois, United States
View deal
Apartment Streeterville
Aug 15 - Aug 22
$484
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with terrace | Close to John Hancock Center | City view

4.8
Outstanding(60 ratings)
Streeterville, Chicago, Illinois, United States
View deal
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

Condo Rogers Park
Jul 7 - Jul 14
$231
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Patio | Perfect for Remote Work

4.7
Excellent(23 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
House Near North Side
Jun 28 - Jul 5
$793
per night
House ∙ 14 guests ∙ 3 bedrooms

Fully Equipped House with Patio | City View

4.7
Excellent(27 ratings)
Near North Side, Chicago, Illinois, United States
View deal
House Fifth City
Apr 28 - May 5
-30%
$279
$173
per night
House ∙ 5 guests ∙ 3 bedrooms

Children-Friendly Beautiful Vacation Home with Garden, Barbeque & Patio | Perfect for Remote Work

4.9
Outstanding(18 ratings)
Fifth City, Chicago, Illinois, United States
View deal
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

House Edgewater Beach
Dec 27 - Jan 3
$389
per night
House ∙ 12 guests ∙ 6 bedrooms

Family-oriented vacation home with terrace & barbecue | Perfect for remote work | Pets are welcome

5.0
Outstanding(4 ratings)
Edgewater Beach, Chicago, Illinois, United States
View deal
Apartment Lake View East
Dec 27 - Jan 3
$412
per night
Apartment ∙ 20 guests ∙ 5 bedrooms

Family-friendly apartment with garden & terrace | City view | Suitable for remote work

5.0
Outstanding(64 ratings)
Lake View East, Chicago, Illinois, United States
View deal
Apartment Ukrainian Village
Mar 23 - Mar 30
$247
per night
Apartment ∙ 10 guests ∙ 4 bedrooms

Child-friendly rental apartment with grill & fast internet

Ukrainian Village, Chicago, Illinois, United States
Free cancellation
View deal

Information about Romantic Getaways in Chicago

😎 Least busy month March
🥳 Busiest month January
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months January and February
🌧️ Rainiest months 9 rainy days in March and April

Romantic Getaways in Chicago: frequently asked questions

Romantic Getaways in Chicago: What is the nightly price for a stay?

HomeToGo offers great vacation homes, with prices as low as $80 per night.

Romantic Getaways in Chicago: does HomeToGo offer a wide variety of vacation homes for groups of guests?

Apartment rental in Chicago on average fits 5 people.

How many couples vacation rentals are available to book in Chicago?

There are more than 11,235 romantic getaways for rent in Chicago with prices starting at $80 per night.

Romantic Getaways in Chicago: what kinds of vacation rentals can I find in Chicago?

Sure, there are 653 House rentals and 2,399 Apartment rentals available in Chicago.

Are there any cheap romantic getaways in Chicago?

One bedroom home rental prices in Chicago start at just $80 and can go up to $719 per night.

Do many rentals in Chicago come with a pool?

Of course, more than 23% of couples accommodations in Chicago come with a pool.

Average Nightly Rental Prices in Chicago

Click on any bar to see price and availability information

Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental availability information in Chicago

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Check out other vacation accommodation options in Chicago

Vacation rentals near Chicago with popular amenities

Check out vacation rentals with popular amenities in Chicago

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