Chicago Travel Guide: Top Things To See, Do & Eat

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(groans) Good morning We gotta catch a flight Let’s go! Hey everyone! Today we’re catching a 2 hour flight out of Toronto to Chicago for our very first weekend in the Windy City [beat-driven music] [flight attendant speaking inaudibly] We made it to Chicago Gotta pick up our bags then check in to the hotel For this trip, we’ve booked a room at the W Chicago City Center We made it to our hotel! Chicago is considered the birthplace of modern architecture and like so many of the businesses downtown the W was converted from a historical building to a modern, stylish hotel that still pays tribute to its roots So it’s raining -I just got in the face by someone’s umbrella Our first stop is a well-known landmark in Chicago Made it to Millennium Park There’s a skating rink and of course a giant bean! Look, I can wear this bean like a hat (laughter) I’ve got a beanie -Punny! Alright, let’s check out the Art Institute of Chicago For this weekend, we’ll be using the Chicago City Pass which gets us access to all the major tourist attractions like The Art Institute of Chicago one of the oldest and largest art museums in the United States There’s stuff you might recognize, and then… I definitely thought this was supposed to be art until I realized that they removed it Looking for Tommy and Cody, where are they? Right over here! Right over here! Our next stop is 360 Chicago in the John Hancock Building which offers views of the city from 94 floors up We made it! We’re going up It was 45 seconds -Oh! (laughter) This is so romantic -Feels super romantic There we are! Oh my God (groaning) We got the best view of the parade Is that a Finding… oh no, that’s not Nemo What is that, a Nutcracker? Now it’s time to grab some food and drinks at the Chicago Athletic Association an upscale hotel in a restored Gothic-style building It’s got various spaces to explore with some amazing food and drinks and you don’t need a be a guest of the hotel to check it out We’ve had a packed first day and I’m so ready to just melt into this bed See you tomorrow! So I just realized I’ve been drinking hot water because I forgot to put my teabag in Oh my goodness (laughter) Oh my God! Woo! It’s chilly in Chicago -Windy City, am I right? Windy City We’re going to go up to the Skydeck Capture some stellar views So, couldn’t go up the tower because it’s too windy Alright, we’re heading to Daly Plaza to check out the Christkindlmarket Woop! We got these cool souvenir decorative mugs I think a leaf just flew into one That’s great! It’s so cold and I double-socked it (laughter) We’re on our way to try a Chicago essential The hot dog! Let’s go! [crowd ambience and music] Alright we’ve got our Chicago-style hot dog We’ve got a lot of different ingredients in there And let’s try to just take a bite (laughter) I ate the whole pepper! My mouth’s on fire! Alright we’re heading to Garrett’s to try some Chicago-style popcorn We’ve got caramel and cheese an interesting combo It’s real cheese! -I don’t want to do this! Cheers! It’s not bad Sweet and savoury -That’s really cheesy Cheese is legit though I would recommend 2 caramel to 1 cheese John just found us the most epic view of the Chicago skyline (screaming) Museum Campus is where you’ll find some of Chicago’s most notable attractions and some great views Navy Pier! We’re going to go up the ferris wheel Let’s go! 3… 2… 1… Thank you! Alright, getting in The ferris wheel at Navy Pier offers some great views of the city and the shoreline but now it’s time for the best part Gonna get deep-dish pizza, but first gotta scarf down these fries we just bought Oh my goodness Oooh Woo! We’re at the bar -This is a Chicago thing, straight up Chicago Alright, we’re going to do this Chicago shot Malört Cheers! Jesus! (laughter) That’s awful! We had such a fun first weekend in Chicago but I know there’s so much more to explore and I’m looking forward to visiting again soon and checking out some of the many neighbourhoods and local experiences that Chicago has to offer Thanks for watching If you liked this video don’t forget to subscribe to gunnarolla on YouTube and check back next week for another adventure


  1. Chicago Athletic Club was a good call, as was Kriskindlmarkt. But on your next visit, try to get out of downtown and into the neighborhoods like : Lincoln Park, Wicker Park, Roscoe Village and Andersonville. On the South Side, check out the Prarie Avenue district, Pilsen, Chinatown, and Bridgeport.
    Also, Chicago Thin Crust pizza!! (It outsells stuffed by 10 to 1 in Chicago).

  2. What a small world! I was in Chicago at the 360 that same day of the parade. We must of cross paths and probably not have noticed.

  3. lol seeing them be skeptical about Carmel and Cheese popcorn is funny to me. As a Chicagoan myself i eat that stuff all the time

  4. Thanks so much for sharing – great content here! I just started my own travel vlog and one of my series is actually a Chicago Guide! Keep up the great work πŸ™‚

  5. They always ignore how bad the shootings, homicides, murders, drugs, human trafficking, gang violence, drive-by shootings, innocent bystanders hit by random bullets, bicycles hit by cars and big rig trucks mostly on the west side, west of the Loop and south side that is south of the Eisenhower Expressway. And also north of Rogers Park around Howard and Clark and Uptown.

  6. my bestfriend lives in chicago and i want to see her and surprise her for her birthday in june i live in orlando florida. we use to go to school together and live in the same apartment complex all i remember was the great moments we had in school it was fun until she moved.

  7. Im planning on going to Michigan(Rothbury) in the summer of 2019 for electric forest but was also thinking of maybe stopping by at Chicago, would you recommend it or would it be too much of a hassle for a one week stay over all.
    Was thinking going to Chicago first for a few days and then finish my trip in Michigan before I would head back to Cali. This would also be my first time on a plane and first trip out of state besides neighboring states around California.

  8. I’m going to Chicago for a bts concert.

  9. I was thinking about visiting O'Block, heard its a nice place to see. After this I will walk through St. Lawrence, some people say I should scream GDK, many there citizens like it and they invite me to smoking some "blunt" filled with L'A pack.

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