Chicago Fun-Times: Hello, Goodbye!

August long weekend should be renamed as the weekend of Music Festivals!   Even though OVO, Veld, Osheaga, and Boots & Hearts were playing in Canada, I decided to head down to Chicago with a couple girlfriends to check out Lollapalooza.  We only went to the festival on the Friday, as it had Eminem headlining and it was all our first time to Chicago, so we also wanted to check out the city.  Boy did the city NOT disappoint!

I didn’t realize how big the Lollapalooza festival was going to be – approx 100,000 capacity vs. Osheaga 40,000 and Veld 85,000.  The highlight of the festival was definitely seeing Eminem who closed on the 1st day.  He also brought out Rhianna as his surprise guest for a couple songs!  Another surprising  thing that happened was we were featured in the Chicago Sun-Times website.  At the the festival a lady came up to us and asked if she could take our picture, then after wrote our names down and mentioned that she was from the Chicago Sun-Times newspaper.  The next day we were shocked to actually see our pictures on the Chicago Sun-Times’ website!  We also had a small celebrity sighting on the first day in Chicago, as we bumped into Barack Obama’s daughter (Malia Obama) at a Walgreens while checking out at the register.  She was paying for her stuff at the till next to us with a couple of her friends.  We guessed that she was in town to go to Lollapalooza, and we guessed right as it seems like she showed up to the music festival on the 3rd day.






The food in Chicago was also on point – I listed some places we checked out below along with the typical Chicago spots that we ventured to!   I found the people so friendly in Chicago – it is definitely a city I’ll come back to again in the near future :).


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Stayed @ Whitehall Hotel = Amazing service and friendly staff!

(Lollapalooza Outfits)
1 snap back hat or hair piece
1 crop top
1 high waisted shorts
1 pair of combat boots or comfy sneakers
1 fanny pack
2 amazing friends to share the unforgettable memories with!


  1. Deep Dish Pizza
    1. [UNO’S] the original deep dish pizza place!  It was cheap only like $10 bucks, but now I understand why people give deep dish pizza mixed reviews.  I’ll let you decide for yourself ;).
    2. Other reco’s we had heard was Giordano’s, Lou Malnati’s, Gino’s
  2. Chicago Popcorn
    1. [Garrett’s] it’s a chain around Chicago that you have to stop into.  There might be lines, but it is definitely worth waiting for!
    2. [Nuts on Clark] stumbled upon this in the airport for my last fix.  It also was good, but I liked the caramel @ Garrett’s better as Garrett’s had a smokey burnt caramel taste.
  3. Chicago Dog
    1.  traditional Chicago-style hot dog (yellow mustard, white onions, bright green relish, dill, pickle spear, tomato slices, pickled peppers, celery salt
    2. [Downtown Dog] this place was close to our hotel and a local spot!  only $3.45 for one traditional Chicago Dog & bag of chips
    3. Locals recommended us to go to Portillo’s or Hot Doug’s but we didn’t have enough time to go, as they were farther from our hotel
    4. Also heard you should check out Wiener Circle post bar and ask for the ladies for the chocolate shake!  lol
  4. Have Brunch
    1. [Yolk] great spot for brunch, but beware of the long lines!  We had to wait approx. 45 minutes before we got a spot.
    2. Dinner reco was Girl & The Goat was recommended but we didn’t have time for dinner spots on our trip


  1. Lollapalooza
    1. Festival was unreal, the venue is massive and the crowds are even massiver!  Prices weren’t crazy either ($6-$8 for a beer and $6-$10 for food).  People were so friendly!
  2. The Bean
    1. Classic tourist picture in Chicago!  A must see thing to do.
  3. The Navy Pier
    1. Cute place to walk around and grab a bite to eat
  4. The Magnificent Mile/Michigan Ave.
    1. Fun street to shop  on and walk around
  5. John Hancock Tower
    1. Go up to the Lounge and buy a drink instead of paying $20 bucks to go up to the viewing tower.  Ladies – make sure to check out the washroom!
  6. Chicago Graffiti
    1. Near Yolk restaurant!  Keep walking down the street as if you’re going to Navy Pier – it’s located under the bridge.  Take a picture of cool graffiti featuring some Chicago team logos.
  7. Go to a Blue’s Bar
    1. [Buddy Guys] had such a cool vibe!  It was a bit of an older crowd, but the live music was amazing ($10-$15 cover).  They even did remixes of Gangam Style and Teach Me How to Dougie!
    2. Locals also recommended Kingston Mines as a good blue’s bar



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