Chicago Things to Do

  • Chicago River Cruise
    Chicago River Cruise
    by riorich55
  • The Bean in Millennium Park
    The Bean in Millennium Park
    by riorich55
  • Serpentine bridge
    Serpentine bridge
    by leics

Most Viewed Things to Do in Chicago

  • 51. Architectural Boat Tour

    We took an Architectural River Cruise. It was a great way to see the city and actually takes you right though the center of it. Chicago has some truly amazing buildings and you get a really good...

    more
  • 52. Chicago Auto Show

    The Chicago Auto Show was first staged in 1901 when the horse and buggy was still the preferred method of individual transportation. But Chicago has always been a bit ahead of its time so it is only...

    more
  • 53. Navigating in Chicago

    If you are like me (yes, I love numbers), you will find this website very useful. The site gives comprehensive demographic information on 77 Chicago community areas....

    more
  • 54. Skyline Boat Tour

    A couple of places offer an Architectural Tour of Chicago via boat on the Chicago River. The tour usually lasts about an hour and is guided. It's an excellent way to see the buildings of Chicago and...

    more
  • 55. Biking

    Along the shores of Lake Michigan in Chicago is a wonderful 18 mile experience. And since Chicago is becoming more and more of a bicycle town and going more toward the path of the late 1800's and...

    more
  • 56. Bus Tours

    The customer service is remarkable and this company is more reliable than the other. Plus being that it is a small group you get to spend more time at the sites and you may get the chance to go to...

    more
  • 57. Pittsfield Building

    The 38-story Pittsfield Building, built in 1927, was Chicago's tallest building at the time, combining Art Deco and Gothic detailing. We stopped by here one day after reading an article about...

    more
  • 58. Robie House

    The Robie House, a fine example of Frank Lloyd Wright's Prairie Style architecture, is located in Hyde Park near the University of Chicago. It was built in 1909 for Frederick Robie and remained a...

    more
  • 59. 333 West Wacker Drive

    As I mentioned in my previous tip, walking along Wacker Drive is the best way to enjoy a great view of the buildings located on the north side of the Chicago River. Even though I can't really say I...

    more
  • 60. Cloud Gate

    Chicago is a great city for learning cultures and enjoying nature. It is pretty in spring, summer, autumn, but cold and windy in winter. I love the city and took some photos to remember its beauty:...

    more
  • 61. James Thompson Center

    I'm not exactly a big fan of "really modern" architecture, but sometimes one such building will strike my fancy. A few examples that come to mind would have to be the "Gherkin" in London, the Pompidou...

    more
  • 62. Corn Skyscrapers

    I must admit that Chicago had more interesting architectural bits & pieces than I had expected. I'm not much into modern architecture (by which i mean anything much later than 1800 or so!) but when...

    more
  • 63. BASKETBALL - Chicago Bulls at the United Center

    Opened in 1994, the United Center is the largest arena in the USA! With over 200 events every year, you can come here to see a great concert or a fun sports event. If you're a sports fan, you may...

    more
  • 64. Rush Street

    Okay, so that was an awful pun, but to get a taste of La Dolce Vita in Chicago take a stroll down Rush Street. This is where the upper classes go to have dinner and hang out. It is the trendy area to...

    more
  • 65. Untouchable Tours

    A good way to see the city is by catching a sight seeing bus with a difference. The Untouchables tour is run by old skool, jazz era, 1920s and 30s 'gangsters' celebrating Chicago's ganster history....

    more
  • 66. Carbide and Carbon Building

    This MetrowalkZ guide can be picked up for free from visitor services in the Cultural Center and Chicago Water Works, and maps out eight fun walks through various parts of the city. They are easy to...

    more
  • 67. FOOTBALL - Chicago Bears at Soldier Field

    Chicago is absolutely the windy city and now I understand why! My husband and I decided to walk to Soldier Field from our hotel (Hilton Chicago on Michigan Ave - a nice walk about 15 minutes) and on...

    more
  • 68. Signature Lounge-Hancock

    Rosie [rozehill] and I went to the Hancock Building, but we did not wish to pay $13.00 for a view of the city. Instead, we rode the rapid elevator to the 96th floor (note that the observation deck for...

    more
  • 69. EL

    I've already discussed this as a "transportation" tip (see that tip for more info and pictures) but it is such a famous and integral part of Chicago's character, and a fun and great way to see the...

    more
  • 70. BASEBALL - Chicago Cubs at Wrigley Field

    Boy, that is a wide open question. I'm from the suburbs of Chicago and have lived here most of my life and I'm still discovering things about Chicago that I never knew before. Here are some brief...

    more
  • 71. Green Mill Cocktail Lounge

    The Green Mill is a bar that Al capone used to use as a club. It is rumoured that there are secret escape passages near the stage area for a quick getaway if required. The bar has been kept as it was...

    more
  • 72. Lake Shore Drive

    Taking a ride on Lake Shore Drive most anytime (except for big snowstorms) is always a great way to see the city of Chicago from another aspect. You can ride along the Lake Michigan shoreline from the...

    more
  • 73. River City

    Every year one day in march, Chicago becomes green... not only their river, but many people wearing green, big green hats, green hair, green everything... It's an irish celebration, i think like...

    more
  • 74. Baha'i Temple

    4.5 out of 5 stars

    Maybe it's my own issues, but going to religious sites, particularly in the US, is often pretty uncomfortable for me. The Mormon Temple in Salt Lake is always bad, and even with historic churches, I...

    more
  • 75. Oak Street Beach

    One of the really nice places to go to enjoy a great view of Lake Michigan is Oak Street Beach. I wasn't too sure at first about walking through the dark pedway that goes underneath Lake Shore Drive...

    more
  • Chicago Hotels

    244 Hotels in Chicago

    6 Reviews

  • Ask a Question

    Got a question about Chicago? Get an answer from our Location locals and frequent travelers

Instant Answers: Chicago

Get an instant answer from local experts and frequent travelers

25 travelers online now

Comments (1)

  • riorich55's Profile Photo
    Mar 19, 2013 at 1:58 PM

    As I was writing some tips for a city just west of where I live this morning I found out about this interesting event happening in June this year.

    I wanted to let anyone who lives in the United States and any visitors to the U.S. this summer that there is a very unique event going on. Lincoln Highway is not as well known as its other old U.S. Highway (Route 66), but is actually older (1913 vs 1926) then its road cousin and actually does travel through the middle of the country from coast to coast (New York to San Francisco). Route 66 actually starts in my hometown of Chicago and heads to California.

    Anyway here is a link and a bit of a description for anybody who is interested. www.lincolnhighwayassoc.org/tour/2013.com

    "Join fellow historians and tourists for the Official Lincoln Highway Centennial Tours, headed for Kearney, Nebraska from each coast, for the centennial of America’s first paved transcontinental road: the Lincoln Highway. Antique cars, Classics, muscle cars, ’50s cars, trucks, motorcycles, street rods, and modern cars are welcome to participate.

    You will travel the original alignments of the Lincoln Highway covering many miles of two-lane history, four-lane progress, and even gravel scenic beauty. Travel from America’s urban centers, through pastoral farm lands, over breathtaking mountains and rolling prairies.

    Travelers from the East will start at Times Square, the heart of America’s most vibrant city. You will travel through ivy-covered college towns such as Princeton, New Jersey, and the Amish country of Pennsylvania. From Pittsburgh’s steel and beer brewing industrial history, you will travel through Ohio’s diverse agricultural and commercial mix. Indiana takes you through more Amish farm land, South Bend’s Notre Dame and automotive history and on to Illinois. From Illinois you will travel to Iowa’s farmland across the Mississippi River into the prairies of Nebraska and on to the Centennial celebration in Kearney at the Great Platte River Arch Museum.

    Western travelers enjoy beginning their journey in the urban centers of San Francisco and Oakland, California. After traveling through the state’s agricultural Central Valley you are exposed to the magnificent Sierra Nevada Mountains and Donner Pass before dropping into the deserts of Nevada and the Great Salt Lake of Utah. Climbing the mountains out of Salt Lake City, you will enter the wide open spaces of Wyoming and on to historic Cheyenne for an overnight stop. This is followed by your easterly trek into Nebraska and eventually joining the rest of the travelers from the east for the grand parade of cars into Kearney on opening day."

Chicago Things to Do

kevinism's Profile Photo

The quintessential American city, Chicago offers world-class culture with zero attitude. You'll see Chicago at its best if you visit during the summer or fall. Summer offers a nonstop selection...

View all Chicago hotels