Chicago, Illinois Vacation Rentals

Apartment | 2 BR | 1 BA | 4 Sleeps

$111 per day

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Apartment | 2 BR | 2 BA | 5 Sleeps

$332 per day

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Apartment | 2 BR | 2 BA | 6 Sleeps

$165 per day

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Apartment | 1 BR | 1 BA | 4 Sleeps

$108 per day

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Apartment | 1 BA | 4 Sleeps

$110 per day

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Apartment | 2 BR | 2 BA | 6 Sleeps

$161 per day

(10)

Apartment | 1 BR | 1 BA | 4 Sleeps

$108 per day

(10)

Apartment | 1 BR | 1 BA | 4 Sleeps

$108 per day

(10)

Apartment | 1 BR | 1 BA | 4 Sleeps

$108 per day

(10)

Apartment | 2 BR | 1 BA | 6 Sleeps

$120 per day

(10)

Apartment | 1 BR | 1 BA | 4 Sleeps

$167 per day

(10)

Apartment | 1 BR | 1 BA | 2 Sleeps

$87 per day

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Apartment | 1 BR | 1 BA | 3 Sleeps

$124 per day

(10)

Condo | 2 BR | 2 BA | 6 Sleeps

$92 per day

(10)

Apartment | 1 BR | 1 BA | 4 Sleeps

$177 per day

(10)

Apartment | 1 BR | 1 BA | 2 Sleeps

$164 per day

(10)

Apartment | 2 BR | 2 BA | 6 Sleeps

$695 per day

(10)

Apartment | 2 BR | 2 BA | 4 Sleeps

$142 per day

(10)

Apartment | 1 BR | 1 BA | 4 Sleeps

$153 per day

(10)

    Why People Visit:

    "Chicago" is thought to be named so after the strong-smelling leeks or wild garlic growing along the Chicago River, and derived from the Native-American Algonquian language version of Ishikawa, translated as “striped skunk” or “smelly onion”. Not a romantic prospect, perhaps, however, the city, fortunately, offers many distractions. What’s not alluring about a lakefront city, rich in diversity and history.

    Known as the Windy City, it’s inextricably synonymous with names immortalized by intriguing crime bosses, Al Capone, Bugs Moran, Dean O’Banion, and Tony Accardo and the FBI’s most wanted, John Dillinger. The Chicago Crime and Mob Tour is a 90-minute coach tour of revelations, visiting many-storied locations including the site of the bloody St. Valentine’s Day Massacre.

    With its strong and pervasive French heritage, food is inevitably among Chicago’s top enticements. Culinary tours abound, and not surprisingly since over 5000 eateries beckon, offering fare reflective of Chicago’s diverse ethnicity. Don’t stop at food, though: coffee and indeed drinks per se are historically tempting. A paradox perhaps in a city so affected by the bygone Prohibition. The Prohibition Tour visits this erstwhile phenomenon and the surreptitious world of the speakeasy.

    The city’s architecture cannot be overlooked, whether or not an appreciator by disposition. The city was remarkably rebuilt after the Great Chicago Fire of 1871 around Lake Michigan and the Chicago and Illinois Rivers, and now offers visitors a spectacle of well-integrated modern and historic buildings.  The Chicago Architectural River Cruise gives a 90-minute perspective from the historic waterway, the Chicago River. With gargoyles peering down over an eclectic mix of past and present, the associated tales only get better with the telling.

    Theaters and museums are among the best in the world, offering live entertainment and opportunities to appreciate the arts and all forms of music. With more than 300 parks, no matter the season or the reason, choices for outdoor activity are bountiful, varied and affordable.

    Vacation the way you want to in Chicago.

    Get There and Get Around:

    Chicago is centrally situated within the United States, and as such easily accessible from anywhere, domestic or international. O'Hare International Airport (ORD) lies an easy 17 miles from downtown Chicago. Midway International Airport (MDW) is the nation's premier point-to-point airport and only 10 miles from downtown Chicago. Chicago Transit Authority’s train (CTA), shuttle buses, taxis, and rideshares conveniently connect both airports to the iconic lakefront, restaurants, community areas, hotels, and your vacation rental.

    Chicago is also accessible via many major interstates and highways. Bus lines, motor coaches and train services connect Chicago throughout the United States and are easy and convenient to use. Choices abound for transportation within the city. Chicago is very much a walking city and the grid system is easily navigable, divided by the State Street/Madison Street intersection. The Chicago Transit Authority (CTA) serves the City and neighboring communities by rail and bus. Chicago's eight ‘L' lines are the most efficient and affordable transportation connecting the city via subway, above-ground, and street-level trains. Two lines run 24 hours-a-day between the airport and downtown, and between the South and North Sides via downtown. Many bus lines also operate 24 hours-a-day with bus stops every few blocks. The Metra commuter rail train provides high-speed connections to the heart of the city, between suburbs and downtown. Taxis are easily accessed or ordered within Chicago, and all accept credit card payments. Water taxis offer a fun alternative to get to popular tourist locations, combining sightseeing with convenience.

    What to Wear (The Weather):

    Summer is bright with festival season, luring visitors with pleasant temperatures and much to do, but also elevated accommodation rates. Chicago is notorious for bitter winters, with frigid temperatures November to March, but accommodation and airfares are more affordable. Be sure to dress for the wind factor which may drop temperatures to below freezing from the average 30s to high 40s. A heavy coat, warm hat, scarf, and gloves are must-haves and you might consider water-resistant snow boots.

    April through May and September through October are the best months to visit, with temperatures between low 50s and mid-80s. Rain is likely so bring a light jacket. These are the best times to catch the festivals and avoid unmanageable crowds. Pack shorts, airy tops, and sandals. Don’t forget sunblock, a cap, sunglasses and water when doing the outdoors in summer. Spring in Chicago requires layers, so pack a windbreaker to throw over light outfits, and remember your umbrella.

    Accommodations

    As would be expected from one of the countries five largest cities, Chicago offers a full range of accommodation types. Downtown hotels (average $150/night), holiday apartments (around $120/night), self-catering units ($140/night), lodges, and Airbnb homestays (from $20/night) are among a few. Outside of the city center options extend to include log cabins and camping spots. Rates vary seasonally, and winter will be the cheapest time of the year, with the greatest availability.

    Things to Do:

    • Winter: Fifth Third Bank Winter WonderFest: 170,000 square feet of attractions and activities

    • Spring: St Patrick’s Day Parade including the dying of the river

    • Grant Park incorporating the Art Institute of Chicago and The Field Museum

    • Lincoln Park Zoo

    • Shop on the Magnificent Mile

    • The Chicago Riverwalk

    • The 606