Chicago Vacation Travel Guide | Expedia

Chicago, once a small trading post on Lake Michigan, has grown into one of the country’s most famous cities. 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. If you’ve worn yourself out in the city proper, 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. Visit our Chicago travel guide and plan your next vacation today.


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Categories: USA & Canada


  1. Maurizio Candido
    Maurizio Candido 12 June, 2016, 01:48

    cicaco la mmerda sulla schifosissima cicaco

    Reply this comment
  2. Maurizio Candido
    Maurizio Candido 12 June, 2016, 01:48

    io Cicaco di notte e di giorno, a seconda di cosa mangio e quando mangio, ma quando cicaco cicaco certi vidozzoli di mmerda da guinnes

    Reply this comment
  3. Fabian Lomeli
    Fabian Lomeli 12 June, 2016, 01:48

    Chicago baby!

    Reply this comment
  4. blkamericano
    blkamericano 12 June, 2016, 01:48

    Was there for memorial weekend one of the best cities I've ever visited!

    Reply this comment
  5. Gabriele Silva De Pinho.
    Gabriele Silva De Pinho. 12 June, 2016, 01:48
  6. Michael Young
    Michael Young 12 June, 2016, 01:48

    I haven't been to Chicago in 6 years I always wanted to go back in visit

    Reply this comment
  7. John Smith
    John Smith 12 June, 2016, 01:48

    Book your hotel in Chicago right now and enjoy early reservation discount

    Reply this comment
  8. TankerUnit Khor
    TankerUnit Khor 12 June, 2016, 01:48

    +Expedia the song is neat, can I download it?

    Reply this comment
  9. Carlos Oliva
    Carlos Oliva 12 June, 2016, 01:48

    aqui de vacaciones muy nice chicago

    Reply this comment
  10. littlelyingliars
    littlelyingliars 12 June, 2016, 01:48

    proud to call Chicago home :)

    Reply this comment
  11. Terry E. Rucks
    Terry E. Rucks 12 June, 2016, 01:48

    I love my city! Lot of people pinpointing the negativity about the Southside of Chicago are ignorant from outside looking in. Crime is every where in every city. I live on the Southside and there so much to do there as well and so much historic heritage it offers. Go to the Science Museum, Dusable African American museum, University of Chicago campus (the Harvard of the Midwest) , Hyde Park (the best neighborhood block in Chicago), as well catch the Chicago White Sox at US Cellular. People don't understand the south side of Chicago actually makes up majority population of Chicago. People enjoy the moment you are in the city and don't always believe what people as well the news media perceive what a city is until you know first hand while you are there. North side Southside and Westside are all Chicago! For those who are coming to Chicago, welcome to the Chi! You are coming to the most laid back city in the world!

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  12. ara blog
    ara blog 12 June, 2016, 01:48
  13. Flashingoutdark
    Flashingoutdark 12 June, 2016, 01:48

    Can you do Tampa, and Jacksonville?

    Reply this comment
  14. Vidisha Roy
    Vidisha Roy 12 June, 2016, 01:48

    My favourite city…loved every inch of it!!!

    Reply this comment
  15. chaosdream1
    chaosdream1 12 June, 2016, 01:48

    cool to have been there, but I prefered florida … so green and clean everywhere, tons of themeparks to walk around all day just chilling:-) love merica, hope I can go back soon.

    Reply this comment
  16. David Martinez
    David Martinez 12 June, 2016, 01:48

    don't forget to visit the south and west side to catch a few bullet holes!

    Reply this comment
  17. bella c
    bella c 12 June, 2016, 01:48

    Proud Chicagoan ??

    Reply this comment
  18. FaZe joshua apex
    FaZe joshua apex 12 June, 2016, 01:48

    Chicago Is Only Like 1-2 Hrs Away From Where I Live..

    Reply this comment
  19. Monstertrkcrzy
    Monstertrkcrzy 12 June, 2016, 01:48

    Could you please make videos for some of the other big cities in the Midwest, like Detroit, the Twin Cities, Cleveland, Cincinnati and Milwaukee? I'm from Texas, but I enjoy watching videos of other great cities around the country.

    Reply this comment
  20. lamraoui yassine
    lamraoui yassine 12 June, 2016, 01:48

    yay 399.999 view

    Reply this comment
  21. BostonianDominican7220
    BostonianDominican7220 12 June, 2016, 01:48

    ChiRaq, where's my boys G Herbo and Lil Bibby?

    Reply this comment
  22. Rai FromThe6ix
    Rai FromThe6ix 12 June, 2016, 01:48
  23. Vincent 0009
    Vincent 0009 12 June, 2016, 01:48

    The weather sucks in general other than than its a nice city

    Reply this comment
  24. Michael Hood
    Michael Hood 12 June, 2016, 01:48

    Hey everyone, I'm starting up a Tumblr page where I'll be posting and reblogging the beds shots of Chicago. For a new view of the best city in the world, follow me on Tumblr, username: mxke .

    Reply this comment
  25. Amy Nangle
    Amy Nangle 12 June, 2016, 01:48

    You didn't talk about the John Hancock Tower

    Reply this comment
  26. The Real Night Hunter
    The Real Night Hunter 12 June, 2016, 01:48

    chicago sucks

    Reply this comment
  27. Franklin Scott
    Franklin Scott 12 June, 2016, 01:48

    I hate Chicago I will never visited there again.

    Reply this comment
  28. Pillow Man
    Pillow Man 12 June, 2016, 01:48

    Don't forget about the best tourist vacation
    now let's hear the reviews
    oh wait they haven't came back!!!!
    that is how much they love CHIRAQ!!!!

    Reply this comment
  29. Moe Flashy
    Moe Flashy 12 June, 2016, 01:48
    TURKISH FARTING 12 June, 2016, 01:48

    oyuufff yoglu syukyulma turklar byutlursan ahuyufff ahyufffflar sikim usa bomblar bomba fyutulmesh byukum

    Reply this comment
  31. Mike Tysh
    Mike Tysh 12 June, 2016, 01:48

    Best parts of Chicago: biking, MCA, and the women! Worst parts: wind+freezing temps & over the top liberals

    Reply this comment
  32. Carmen Quiles
    Carmen Quiles 12 June, 2016, 01:48

    When you visit us don't miss The Chicago Architectural Tour on the River. For awesome Chicago Blues find Rosa's Lounge. It has family appeal and is not a tourist trap.

    Reply this comment
  33. saleh mohmad
    saleh mohmad 12 June, 2016, 01:48
  34. SomeNewYorker
    SomeNewYorker 12 June, 2016, 01:48

    im from NYC i plan to be an architect and my BIGGEST dream is to shape the city of Chicago………

    it's so beautiful

    Reply this comment
  35. cristina Lopes
    cristina Lopes 12 June, 2016, 01:48

    NYC I love Chicago

    Reply this comment

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