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Romantic Getaways in Chicago

Chicago
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$100 - $199
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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

Apartment West Ridge
Feb 3 - Feb 10
$50 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in West Ridge

West Ridge, Chicago, Illinois, United States
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House Goose Island
Dec 2 - Dec 9
-37%
$281
$176 per night
House ∙ 14 guests ∙ 3 bedrooms

Charming Vacation Home in Goose Island with Sauna & Grill

4.9
Outstanding (48 ratings)
Goose Island, Chicago, Illinois, United States
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Apartment Washington Park
Dec 2 - Dec 9
$99 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment in Washington Park

Washington Park, Chicago, Illinois, United States
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House Palmer Square
Feb 3 - Feb 10
$350 per night
House ∙ 10 guests ∙ 5 bedrooms

Wonderful House in Palmer Square with Grill

3.4
(6 ratings)
Palmer Square, Chicago, Illinois, United States
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Apartment Near North
Jan 13 - Jan 20
-29%
$266
$188 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Near North, Next to John Hancock Center

4.7
Excellent (3 ratings)
Near North, Chicago, Illinois, United States
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House Douglas
Dec 9 - Dec 16
-80%
$460
$91 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Douglas

3.9
Good (21 ratings)
Douglas, Chicago, Illinois, United States
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House Beverly
Dec 9 - Dec 16
-32%
$295
$200 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Beverly with Grill

3.0
(12 ratings)
Beverly, Chicago, Illinois, United States
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Apartment Washington Park
Nov 30 - Dec 7
$120 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Rental Apartment in Washington Park

Washington Park, Chicago, Illinois, United States
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Apartment Tri-Taylor
Jan 13 - Jan 20
-63%
$304
$111 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Tri-Taylor

Tri-Taylor, 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 West Ridge
Feb 3 - Feb 10
$50 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in West Ridge

West Ridge, Chicago, Illinois, United States
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House Beverly
Dec 9 - Dec 16
-32%
$295
$200 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Beverly with Grill

3.0
(12 ratings)
Beverly, Chicago, Illinois, United States
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Apartment Washington Park
Nov 30 - Dec 7
$120 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Rental Apartment in Washington Park

Washington Park, Chicago, Illinois, United States
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Apartment Tri-Taylor
Jan 13 - Jan 20
-63%
$304
$111 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
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House Goose Island
Dec 2 - Dec 9
-37%
$281
$176 per night
House ∙ 14 guests ∙ 3 bedrooms

Charming Vacation Home in Goose Island with Sauna & Grill

4.9
Outstanding (48 ratings)
Goose Island, Chicago, Illinois, United States
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Apartment Fulton Market
Oct 19 - Oct 26
$1,526 per night
Apartment ∙ 24 guests ∙ 6 bedrooms

Apartment in Fulton Market with Overnight Parking

4.9
Outstanding (12 ratings)
Fulton Market, Chicago, Illinois, United States
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Apartment Ukrainian Village
Dec 19 - Dec 26
-52%
$662
$315 per night
Apartment ∙ 10 guests ∙ 4 bedrooms

Charming Apartment in Ukrainian Village with Private Balcony + Skyline Views

5.0
Outstanding (9 ratings)
Ukrainian Village, Chicago, Illinois, United States
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Apartment Heart of Chicago
Feb 16 - Feb 23
-56%
$217
$95 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Entire Apartment in Heart Of Chicago

5.0
Outstanding (72 ratings)
Heart of Chicago, Chicago, Illinois, United States
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House Douglas
Dec 9 - Dec 16
-80%
$460
$91 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Douglas

3.9
Good (21 ratings)
Douglas, 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

Apartment Palmer Square
Nov 30 - Dec 7
-69%
$191
$59 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Entire Rental Apartment in Palmer Square with Free Parking

3.9
Good (20 ratings)
Palmer Square, Chicago, Illinois, United States
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Apartment Wrigleyville
Jan 2 - Jan 9
-58%
$270
$113 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Stylish Rental Apartment in Wrigleyville + Lake View

4.4
Very good (17 ratings)
Wrigleyville, Chicago, Illinois, United States
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House East Village
Feb 2 - Feb 9
-38%
$627
$389 per night
House ∙ 12 guests ∙ 4 bedrooms

House in East Village + Skyline Views

5.0
Outstanding (3 ratings)
East Village, Chicago, Illinois, United States
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Apartment North Center
Jan 1 - Jan 8
-36%
$203
$129 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Bright Rental Apartment in North Center

4.0
Very good (29 ratings)
North Center, Chicago, Illinois, United States
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House Cragin
Mar 2 - Mar 9
-53%
$847
$401 per night
House ∙ 16 guests ∙ 7 bedrooms

Wonderful Vacation Home in Cragin with Yard

3.7
Good (3 ratings)
Cragin, Chicago, Illinois, United States
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Condo Austin
Feb 3 - Feb 10
$133 per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo in Austin

4.6
Excellent (31 ratings)
Austin, Chicago, Illinois, United States
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House River North
Dec 16 - Dec 23
-44%
$393
$219 per night
House ∙ 8 guests ∙ 2 bedrooms

House in River North with Private Parking, Next to Magnificent Mile + Panoramic Views

River North, Chicago, Illinois, United States
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House Washington Park
Jan 13 - Jan 20
-67%
$1,007
$332 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Washington Park with Yard

Washington Park, Chicago, Illinois, United States
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House Bronzeville
Mar 2 - Mar 9
$545 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Bronzeville

4.7
Excellent (12 ratings)
Bronzeville, 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

Condo West Lakeview
Nov 30 - Dec 7
-66%
$355
$123 per night
Condo ∙ 9 guests ∙ 3 bedrooms

Condo in West Lakeview

4.4
Very good (6 ratings)
West Lakeview, Chicago, Illinois, United States
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Apartment Back of the Yards
Nov 30 - Dec 7
$96 per night
Apartment ∙ 5 guests ∙ 1 bedroom

Apartment in Back Of The Yards with Spacious Garden

3.8
Good (5 ratings)
Back of the Yards, Chicago, Illinois, United States
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Apartment Pilsen
Dec 2 - Dec 9
-65%
$265
$92 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental Apartment in Pilsen

5.0
Outstanding (1 rating)
Pilsen, Chicago, Illinois, United States
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Apartment Greater Grand Crossing
Mar 2 - Mar 9
-40%
$159
$95 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Greater Grand Crossing

Greater Grand Crossing, Chicago, Illinois, United States
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Apartment Brighton Park
Jan 13 - Jan 20
$70 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment in Brighton Park with Yard

4.6
Excellent (7 ratings)
Brighton Park, Chicago, Illinois, United States
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Apartment Logan Square
Mar 2 - Mar 9
-43%
$150
$85 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Pleasant Rental Apartment in Logan Square with Yard

4.7
Excellent (70 ratings)
Logan Square, Chicago, Illinois, United States
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House Bridgeport
Jan 5 - Jan 12
-30%
$814
$570 per night
House ∙ 17 guests ∙ 6 bedrooms

Family Friendly Vacation Home in Bridgeport with Delightful Barbecue

4.7
Excellent (3 ratings)
Bridgeport, Chicago, Illinois, United States
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House Near West Side
Dec 15 - Dec 22
-28%
$407
$292 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Near West Side with Electric Fireplace

5.0
Outstanding (44 ratings)
Near West Side, Chicago, Illinois, United States
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Apartment Pilsen
Dec 1 - Dec 8
-37%
$210
$133 per night
Apartment ∙ 5 guests ∙ 3 bedrooms

Apartment in Pilsen

5.0
Outstanding (12 ratings)
Pilsen, Chicago, Illinois, United States
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Information about Romantic Getaways in Chicago

😎 Least busy month December
🥳 Busiest month November
🛏️ 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

Frequently Asked Questions

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

You can find more than 9,411 homes to rent in Chicago with prices starting at $50 per night.

What kinds of vacation rentals can I find for Romantic Getaways in Chicago?

You can choose from 549 House rental and 2,024 Apartment rental for Romantic Getaways in Chicago right here on HomeToGo.

Romantic Getaways in Chicago: What is the cost per night?

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

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

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

Are there any cheap couple's getaways in Chicago?

Couples home rental prices in Chicago start at just $50 and can go up to $590 per night.

Can you find vacation homes in Chicago offer a pool?

Definitely, over 25% of couples accommodations in Chicago offer a pool.

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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

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