Top Destinations for a Weekend Getaway in Chicago - HomeToGo base64Hash Top Destinations for a Weekend Getaway in Chicago - HomeToGo

Top Destinations for a Weekend Getaway in Chicago

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Weekend Getaway in Chicago: Recommended rentals

Weekend Getaway in Chicago: find your perfect rental from just $46 per night!

Bed and breakfast River North
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Beautiful bed & breakfast with 1 room for 2 persons

River North, Chicago, Illinois, United States
from $107
per night
from $107
per night
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Bed and breakfast Magnolia Glen
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Nice bed and breakfast with garden, patio & pool

Magnolia Glen, Chicago, Illinois, United States
from $224
per night
Outstanding
from $224
per night
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Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with 1 room for 2 persons

West Woodlawn, Chicago, Illinois, United States
from $83
per night
from $83
per night
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Bed and breakfast Roscoe Village
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

Fully equipped pleasant bed and breakfast with yard & patio | Good for workation

Roscoe Village, Chicago, Illinois, United States
from $229
per night
Outstanding(158 ratings)
from $229
per night
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Bed and breakfast Roscoe Village
Bed and breakfast ∙ 2 guests ∙ 2 bedrooms

Family-oriented charming B&B with patio & yard

Roscoe Village, Chicago, Illinois, United States
from $347
per night
Outstanding(104 ratings)
from $347
per night
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Bed and breakfast Rogers Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with yard

Rogers Park, Chicago, Illinois, United States
from $72
per night
Excellent
from $72
per night
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Bed and breakfast Bronzeville
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed and breakfast with 1 room for 2 persons

Bronzeville, Chicago, Illinois, United States
from $104
per night
from $104
per night
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Bed and breakfast Legends South
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Bed & breakfast with yard

Legends South, Chicago, Illinois, United States
from $144
per night
Very good
from $144
per night
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Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented wonderful bed and breakfast with terrace & garden | Suitable for remote work | Pets are welcome

Bucktown, Chicago, Illinois, United States
from $218
per night
Outstanding(341 ratings)
from $218
per night
View deal
Bed and breakfast Avondale
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

B&B for 4 persons

Avondale, Chicago, Illinois, United States
from $169
per night
from $169
per night
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Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with patio & garden

West Woodlawn, Chicago, Illinois, United States
from $83
per night
from $83
per night
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Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed & breakfast with terrace, barbeque & yard | Good for workation

Sheffield Neighbors, Chicago, Illinois, United States
from $271
per night
Excellent(99 ratings)
from $271
per night
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Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

B&B with patio, jacuzzi & yard

Sheffield & DePaul, Chicago, Illinois, United States
from $279
per night
Good
from $279
per night
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Bed and breakfast Logan Square
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Bed & breakfast with yard & terrace

Logan Square, Chicago, Illinois, United States
from $188
per night
from $188
per night
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Bed and breakfast South Austin
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with 1 room for 2 persons

South Austin, Chicago, Illinois, United States
from $131
per night
from $131
per night
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Planning a Weekend Getaway in Chicago

Famous for its deep-dish pizza and hot dogs, America's Windy City makes for the perfect adventure. Its fantastical architecture, jazz and blues culture, world-class museums, and festivals are second to none. A weekend getaway will prove unforgettable.
What to Do in Chicago

What to Do in Chicago

There's much to see and do in Chicago, from checking out artworks by the Grand Masters to soaking up surreal architecture and savoring legendary food. The nightlife is more than just nightclubs – head out to see for yourself!

  • 1. Museum hopping

    A great place to start your weekend is at the Museum Campus, which houses the Adler Planetarium, the Field Museum, and the Shedd Aquarium, all within walking distance of each other. The Museum of Science and Industry (or MSI) is the western hemisphere's largest museum, while Chicago’s Museum of Contemporary Art and Art Institute are home to works by heavyweights such as Warhol and Monet.

  • 2. Chicago river boat architecture tour

    In Chicago, centuries-old architectural styles meet futuristic designs. The architecture cruise along the Chicago River introduces you to all styles: Art Deco, neoclassical, Gothic, and of course, towering steel skyscrapers. Learn all about Chicago's skyline with specialist guides.

  • 3. Signature Chicago food

    Try classic deep-dish Chicago pizza with a buttery crust and topped with melted cheese, or a Chicago Italian beef sandwich – it can be ordered dry, wet, or dripping wet! Another must for gastronomes is the Chicago hot dog, a Viennese sausage stuffed into a poppy seed bun. The best are rumored to be Portillo's. Feeling adventurous? Try Malört, a wormwood-based drink brought to Chicago in the 1930s by a Swedish immigrant.

  • 4. Nighttime entertainment

    Swing by the Green Mill (opened as Pop Morse's Roadhouse in 1907), a late-night jazz club that was patronized by gangster Al Capone. Marvel at the city's skyline from SkyDeck Chicago and the John Hancock 360 Observatory, or just take an evening helicopter tour. The Chicago Riverwalk makes for a romantic stroll, as does the eco-friendly Chicago Segway Night Tour, which glides by prominent illuminated landmarks.

Best Places to Stay for City Breaks in Chicago

Bed and breakfast Andersonville
from $85
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

3.6
Good
Andersonville, Chicago, Illinois, United States
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Bed and breakfast University Village / Little Italy
from $228
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

University Village / Little Italy, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $254
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace, BBQ & garden | Suitable for remote work

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
View deal
Day Trips from Chicago

Day Trips from Chicago

You'll soon notice that Chicago is a great launching point for day trips to neighboring states, thanks to its excellent transport connectivity and strategic location. Take your pick from sleepy riverside towns and European-style communities right in America.

  • 1. Milwaukee

    Less than two hours away from Chicago is Milwaukee, hailed for its German brewing prowess and farm-to-table restaurants. The City of Festivals is also home to the world's only Harley Davidson Museum and over 75 golf courses.

  • 2. Holland, Michigan

    Can't visit the Netherlands? No problem, drive to this Holland to experience Dutch heritage. Top attractions include the Veldheer Tulip Gardens and Windmill Island Gardens. The Dutch architecture, cuisine, and ubiquitous windmills make for Instagram-worthy pictures.

  • 3. Kettle Moraine State Forest

    Less than three hours away from Chicago, this 30,000-acre forest offers opportunities for horse riding, hiking and mountain biking, skiing, and snowshoeing. Look out for historical sites such as Old World Wisconsin Outdoor Museum, Wade House Stagecoach Inn, and Holy Hill Basilica.

  • 4. Lake Geneva

    You've seen Holland, now make way for Switzerland in this Wisconsin city one hour and 40 minutes from Chicago. Cycle along the picturesque, windswept Lake Geneva Shore Path and check out the eclectic nightlife options, restaurants, and independently owned shops.

  • 5. North Utica

    Nestled along the Illinois-Michigan canal and Illinois River, this bucolic river town is all about antique and collectible shops, wineries, flea markets, and pottery studios. Trace the town's eventful history at the LaSalle County Historical Museum.

Recommended Accommodations for City Breaks in Chicago

Bed and breakfast Near West Side
from $219
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast for 2 persons

Near West Side, Chicago, Illinois, United States
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Bed and breakfast West Woodlawn
from $87
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with barbecue, patio & yard

4.8
Outstanding
West Woodlawn, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from $198
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented spacious B&B with patio & yard | Good for workation | Pets allowed

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
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What to Pack for Your Weekend Getaway in Chicago

What to Pack for Your Weekend Getaway in Chicago

What you pack will depend on the season you plan to visit. It goes without saying that a light jacket will always come in handy in the Windy City.

  • 1. Smart casual wear

    Chances are you'll be bar hopping, attending a Broadway show, or listening to extended blues sessions at a nightclub. Dress the part and fit in with the crowd for a fun time. A denim jacket, jeans, and dressy shoes are a great idea.

  • 2. Sun protection

    The sun shines brightly in Chicago, but sunscreen, good quality sunglasses, and a wide-brim hat will protect you. A refillable water bottle is recommended to keep from being dehydrated.

  • 3. Comfortable walking shoes

    You'll need a comfy pair of shoes for all those hours spent in museums, parks, and at the clubs. Those planning day trips that involve swimming or hiking should bring along appropriate footwear and a swimsuit.

  • 4. Layered clothes

    Bring layers along. A light jacket and shawl will do in the warmer months. Meanwhile, winters demand something heavier, such as a down jacket, thermal underclothes, warm socks, and a wool hat.

Top Offers for City Breaks in Chicago

Bed and breakfast Near West Side
from $140
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming B&B for 2 persons

Near West Side, Chicago, Illinois, United States
View deal
Bed and breakfast West Loop
from $363
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
View deal
Bed and breakfast West Loop
from $309
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Information about Weekend Getaway in Chicago

💳 Highest rates in May
🥳 Busiest month January
🛏️ Popular home types Apartment rental and Bed and breakfast rental
🌡️ Hottest months July and August
❄️ Coldest months 17 °F in January and February
🌧️ Rainiest months 9 rainy days in March and April
54,612 reviews
Chicago vacation rentals have an average rating of 4.4/5 on 54,612 reviews left by travelers.

Weekend Getaway in Chicago: frequently asked questions

Weekend Getaway in Chicago: What is the nightly cost of a stay?

HomeToGo offers incredible vacation rentals, with rates as low as $46 per night.

Weekend Getaway in Chicago: can I find a vacation rental suitable for a group?

Bed and breakfast rental in Chicago can fit 3 guests.

How many vacation homes are available to rent for a weekend in Chicago?

There are more than 5,467 city break accommodations available in Chicago with prices starting at $46 per night.

Weekend Getaway in Chicago: what kinds of vacation rentals can I find in Chicago?

There are 84 Bed and breakfast rentals and 166 Apartment rentals available in Chicago.

How much does it cost to take a weekend getaway in Chicago?

The cost of a vacation home in Chicago for the weekend can start from $46 and can go up to $449 per night.

Do many accommodations in Chicago offer a pool?

Yes, over 33% accommodations in Chicago come with a pool.

Check out more vacation options

Check out other vacation accommodation options in Chicago

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