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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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.

City Breaks in Chicago: Top Accommodations

House Grand Boulevard
Aug 12 - Aug 19
$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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Apartment West Town
Jul 21 - Jul 28
$255 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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Apartment Ukrainian Village
Aug 12 - Aug 19
$680 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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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

Condo Lake View
Apr 1 - Apr 8
-26%
$416
$307 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Lake View with Patio & Grill

Lake View, Chicago, Illinois, United States
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Apartment Humboldt Park
Apr 1 - Apr 8
$115 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Humboldt Park with Yard & Patio

4.5
Excellent (66 ratings)
Humboldt Park, Chicago, Illinois, United States
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Apartment South Austin
Jun 22 - Jun 29
$111 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in South Austin

South Austin, Chicago, Illinois, United States
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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

Apartment Lake View East
Jun 25 - Jul 2
$720 per night
Apartment ∙ 16 guests ∙ 4 bedrooms

Charming Rental Apartment in Lake View East with Patio & Grill

5.0
Outstanding (96 ratings)
Lake View East, Chicago, Illinois, United States
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House Near North Side
Apr 24 - May 1
-71%
$285
$83 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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House Bronzeville
Apr 1 - Apr 8
$550 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Bronzeville with Patio

4.8
Outstanding (13 ratings)
Bronzeville, 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

House Humboldt Park
Apr 1 - Apr 8
$68 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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Apartment Grand Boulevard
Apr 1 - Apr 8
$190 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Beautiful Apartment in Grand Boulevard with Yard

4.2
Very good (11 ratings)
Grand Boulevard, Chicago, Illinois, United States
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House Grand Boulevard
Aug 12 - Aug 19
$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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Information about Weekend Getaway in Chicago

😎 Least busy month June
🥳 Busiest month February
🛏️ 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 9 rainy days in March and April

Frequently Asked Questions

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

You can get a great vacation rental for somewhere between $123 and $724 and find discounts up to 39%!

Can I find a vacation rental for a group of guests for Weekend Getaway in Chicago?

Usually the size of a Apartment rental is 85 m² and can fit 4 people on average which is great for medium-sized groups and families.

How many accommodations are available to rent for a weekend getaway in Chicago?

There are more than 9,960 city break rentals available in Chicago with prices starting at $66 per night.

What kinds of vacation rentals can i book for Weekend Getaway in Chicago?

We would suggest browsing our incredible selection of House rental and Apartment rental for Weekend Getaway in Chicago.

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

The cost of a vacation rental in Chicago for the weekend can range from $66 and can go up to $724 per night.

Do many vacation rentals in Chicago come with a pool?

Absolutely, more than 24% accommodations in Chicago come with a pool.

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Average Nightly Rental Prices in Chicago

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Vacation Rental Price Information in Chicago

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