32° - January
38° - February
47° - March
59° - April
70° - May
80° - June
84° - July
83° - August
76° - September
64° - October
49° - November
37° - December
Dec avg
Avg Hotel
Est. Airfare

Best Known For


The historic Chicago, home to the 1933 World Fair, Al Capone, and jazz music, is ethnic, diverse and enchantingly vibrant. It's a one of a kind city with so much to do, you'll never possibly do or see it all. It's also the kind of city with such delicious food that you could spend your entire vacation eating and not regret it for a moment. The pizza, sandwiches, and even hot dogs are both unique and fabulous in Chicago. The Windy City loves visitors so much that they offer a variety of activities for free. And as if this booming metropolis doesn't already have enough, Lake Michigan adds adventure and water sports to the equation.
Photo Credit: Marian Kraus Photography
  • W Chicago City Center

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  • Ritz Carlton Chicago by Four Seasons

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  • Chicago Hilton

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    We Have It Here

    Anything you might want to do, you can do it in Chicago. We have world renown theater, museums, dance, dining and sports. The only reason I did not give it 5 stars is because the temperature in February can get a bit nippy. That being said, hotel rooms are cheap that month and most of the locals are still out and about, enjoying good food and fine arts. Just dress warm.

    If you come in the warm weather, bring your swim suit. Newcomers are always surprised at how much we use our beaches and the extensive parks along the Lake.

    There are so many local resources, include local blogs like so use it to plan your passion.

    To help keep your bearings, remember where the lake is. It is always east of you.
    Use public transportation. All the locals do so buy a 3-day pass and get your money's worth!

    Birthplace of the skyscraper

    Chicago is impressive. So many skyscrapers looking down on you, it does something to a man. My favorites are the Devil's Towers. A sight for sore eyes at night! Walking through the centre you will see one beauty after another. The Bean, one of the tourists' favorite places, is definitely something else. The Navy Pier has a very special charm. Fountains, buildings, monuments, skyscrapers, shops... This is the place to be!

    All American Pride

    If you want to experience what being an American is like, Chicago is your city. There is a sense of pride around the industrial working, blue jean wearing, hot dog and pizza eating culture that defines this city. Coupled with the good food is a history of social justices, mob bosses, and riots that you can see remnants of in this now-safe city. The third largest city in America, it is more manageable then New York and offers a more local vibe.

    During the summer time Chicago becomes a robust affordable city to experience free concerts in, go on walking tours, and lounge by the great lakes of America. Culturally rich, you will benefit by considering a visit during sports season for baseball or basketball. Adding to the American culture, the loyalty to sports here is matched only by its neighboring cities. This is a place to tour in the morning, sail in the afternoon, and go to a game at night.

    The architecture is rich with aged buildings peppered in modern art installations that are plentiful and attractive. When you are in Chicago, you know the city itself wants you to have a good time. They want you to lounge in the greatest city in the Midwest, as you should. They will cater to your budget to spend as little or as much as you like without compromising on the city experience.

    A family friendly local, Chicago attracts some of the most notable culture in America. Though the art is there, I don't reference this city as a dance or music mecca. To me, it is known as the All-American city where it feels good to see what can become.

    Displaced Native Chicagoan Reviews the City

    I grew up just outside of Chicago but now only return on vacation and to visit family. Chicago is a great city that has something for everyone. If you are going during the summer months be sure to check out Navy Pier, any number of music or arts festivals that are happening, catch a ball game and visit one of the many museums the city has to offer. If you are travelling with kids, make sure to make a visit to the Field Museum. Not only does it have a solid collection of exhibitions of its own, they also frequently get internationally renowned travelling exhibitions. If you like wandering around looking at buildings, consider taking an architectural tour of the city or a river boat tour.

    If you are travelling to Chicago during the winter, be prepared for windy chills! Plan on spending a good time indoors but don't miss checking out the Millennium Park ice rink at night. Lines will be long but its a fantastic (and romantic) experience with the skyline lit up in the background. If you are into the craft beer scene, Chicago has a number of local breweries. Check out Revolution Brewery for a tour of how they make their craft beer, sample a drought and then head over to their restaurant for some delicious food and beer pairings.

    Chicago is a city of many sides and offers a diversity of travel activities year-round. Best advice is plan ahead but leave room for some spontaneity, you'll never know what you may discover while you're visiting.

    My Kind of Town

    With the city filled with summer festivals and free concerts every week May through September, you are not trying if you find yourself with nothing to do in Chicago. The rest of the year can be just as fun, but you have to dig a little deeper and bare the cold to find the free museum days and ice skating rinks throughout the city.

    It is a city that has all to offer; with great restaurants for all tastes and price ranges. You can catch a concert from any genre or sit back and enjoy the theater or dance any time of the year. And if none of that is your taste, this city loves their sports teams! You can catch a game at the classic Wrigley Field or watch the 2013 Stanley Cup Champions Chicago Blackhawks. There is something for everyone regardless of your vacation price tag.

    It is easy to get around the city without driving. The CTA (Chicago's Transit Authority) has an easy to follow 'L' Train (Elevated/Subway Train) and Bus system where you can buy 3 day or 7 day passes. Summer of 2013, they released their newest transit option - DIVVY; shared bike stations. You pick up an drop off your bikes at stations throughout the city and costs only $7 a day to rent.

    Any Day, Any Time of the Year - It's My Kind of Town
    great place to visit. good food, great landmarks, beware of the cold if u are travelling between nov to april
    if you like city living, this is for you.
    shopping is one of the most popular activities in chicago.
    Hancock, Sears, Navy Pier, Medieveil Times, American Girl, Hershey, and of course Chicago style pizza
    Chicago has some of the best food in the world, both in the fine dining aspect and the street food. Way better architecture than New York too!
    Chicago is a blast...any time of year. This city has so much to offer. Shopping, food, PIZZA!, hockey games, the Shedd Aquarium, the John Hancock Building, Milennium Park...I could go on and on.
    When we were there, we did all of the above. Michigan Avenue shopping is superb. My favorite store for great deals is Filene's Basement. I bought my husband a $300 Calvin Klein wool pea coat there for $70!
    My absolut favorite restaurant in Chicago is Bistro 110. They have a fabulous menu, with everything from chicken to escargot. Their creme brulee and chocolate mousse on the dessert menu are to do for. What a romantic atmosphere as well. Cost is about $100 per couple with alcoholic drinks.

    Lincoln Park Zoo

    Lincoln Park Zoo is a free 35-acre zoo located in Lincoln Park in Chicago, Illinois. The zoo was founded in 1868, making it one of the oldest zoos in the nation.
    Cost: Free

    Navy Pier

    Navy Pier is a 3,300-foot long pier on the Chicago shoreline of Lake Michigan and is now a shopping and entertainment attraction
    Cost: Free

    Millennium Park

    Discover a state-of-the-art collection of architecture, landscape design and art that provide the backdrop for hundreds of free cultural programs including concerts, exhibitions, tours, and family activities.
    Cost: Free


    The Sears tower, planetariums, museums, famous homes and so much more.
    Cost: Varies By Attraction
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    Go Chicago Card

    To see all of the best Chicago attractions and participate in the most popular Chicago tours, the Go Chicago Card is one of the best deals in Chicago.
    Cost: 1 Day-$66.99 Adult/$44.99 Child
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    Sports Venues

    Historic Wrigley Field-home to the Cubs, Soldier Field-home to the "Da Bears". US Cellular Field-home to the White Sox, United Center home to the Bulls and more
    Cost: Varies
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    Free Activities in Chicago

    • Navy Pier: Strolling the Navy Pier costs nothing, but even more free attractions are located onsite. Performances are held at both indoor and outdoor venues at the pier, and fireworks light the sky twice weekly during summer, all at no cost. • Crystal Gardens at Navy Pier: If it's not in use for an event, enjoy taking a rest in this glass ballroom containing open seating and dancing fountains. It's a well-kept secret mostly frequented by residents, so it's a great place to get a break from the crowds. • Smith Museum of Stained Glass Windows at Navy Pier: light streams through colorful and awe-inspiring works of art. • Millennium Park: Take your photo in front of the shiny, stainless steel Cloud Gate sculpture or at the innovative Crown Fountain, where projected images of faces are positioned so that water appears to flow from their mouths. The park also occasionally hosts free live performances. Lurie Gardens is also nearby and a lovely place to stroll. • Lincoln Park Zoo: The city's renowned 35-acre Lincoln Park Zoo is free too. As one of the oldest zoos in the United States, it provides a world-class atmosphere for learning about wildlife.
    Cost: FREE




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    O'Hare International Airport [ORD]
    Midway Airport [MDW]