Chicago Vacation Travel Guide | Expedia

Chicago – From humble beginnings, this city has bloomed into one of the USA’s frontrunners. Check out the top sights in Chicago and start planning a trip!

When ready, browse vacation packages to Chicago:

#Chicago, once a small trading post on Lake Michigan, has grown into a true global city. Visit “The Windy City” and chow down on deep dish pizza for a truly unique #vacation experience.

Follow “The Loop,” the city’s primary business district, and marvel at its array of high-rise buildings, consulates, and universities. Shopping and fine dining abound in this area. Set a more sedate pace at the Riverwalk, a pedestrian path along the Chicago River, or #visit the many museums and parks the city has to offer. You’ll never believe you’re actually downtown when you walk through the Garfield Park Conservatory, and the Art Institute of Chicago will allow you to appreciate creative works from around the world.

No Chicago #tour is complete without a mention of the nightlife, so close out your day at a jazz lounge and let the sweet sound of music carry you away.

For now, we hope you enjoy watching this #travel #guide as much as we enjoyed making it.

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0:00 – Chicago
0:55 – The Loop
1:13 – Willis Tower
1:43 – Magnificent Mile
1:53 – Old Water Tower
2:17 – The Riverwalk
2:30 – Millennium Park
3:04 – The Art Institute of Chicago
3:22 – Garfield Park Conservatory
3:40 – Frank Lloyd Wright’s home and studio
3:51 – Unity Temple
4:02 – Birthplace home of Ernest Hemingway
4:18 – Navy Pier
4:29 – The Field Museum
4:54 – Museum of Science and Industry
5:16 – Lincoln Park
5:36 – Lincoln Park Zoo
5:51 – Chicago History Museum


  1. Go indoors — to the Cultural Center (Michigan and Randolph), the Railway Exchange Building (Michigan between Jackson and Adams), or the Palmer House lobby and look around you and understand what civic pride used to be.

  2. 1:44 That building with the clock tower is Marshall Fields Department Store which is now currently Macy's, It was famous back in the day for Christmas displays and quality service.

  3. Chicago was my second trip to America and I loved it, it really is an amazing city.
    Best part is seeing Sue and the Tsavo Man-Eaters in the Field Museum.
    That was August of 2012 and I can still remember how it felt to be in that awesome American city.

  4. 6:07 Yeaaah, surrrrrrrrre. The downtown doesn't look very bright at all to me. As a matter of fact, Downtown Chicago is a ghost town at night because Nobody really resides in the downtown area, they only commute from the surrounding suburbs. New York City truly lights up when the sun sets, NOT Chicago.

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  6. This is 90% downtown, and the other 10% is Lincoln Park, the Field Museum and the suburbs (Oak Park). For a city that is primarily neighborhood based (and nobody lives downtown), this doesn’t represent all of what Chicago has to offer.

  7. Looks like there is so much to check out around where you made this video. How often do you visit this particular area? Please join us too on our travels around fun places in Singapore. 🙂 Hope to see more from you.

  8. I use to live in Chicago and it's the most racist and segregated city in America. People don't talk about that, but it being divided and racist is an understatement.
    Very beautiful fun city, but I found the south to be more accepting than that place.

  9. Been living close to Boston for last 14 years and traveled about 35 States. Chicago sure is on my favorite Cities to live or visit during summer.

    #1 Chicago
    #2 Boston
    #3 ….Hmm no its not NYC.

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