Travel Guide: The Best Chicago Trip

I am a huge fan of city life – I always have been. Obviously New York is pretty much my favorite place on earth, but after last weekend, I have to say that Chicago is up there. I personally have been to Chicago a few times and every trip is different. This past trip in particular was my favorite trip I have taken there, so I wanted to break down what I did and where I went because I think all of you should go there now. ­čÖé

Day One:

Surprise Birthday Party for a friend at Fulton Market KitchenKC and KellyThis space was amazing. It’s an old warehouse, made restaurant, with walls of exposed brick and amazing local street artist. Chill, lounge, dark vibes and really good food. We also had an amazing DJ, so a dance party definitely happened.KC Party Look

Day Two:

Day two was mostly a hotel day since the hotel we stayed in was completely badass. I am in now officially in love with the London House Hotel. From decor down to the gym, everything is perfect. Plus they offer great rates during the off season, which is always nice. Day two we ordered room service, where I had quite literally the best blueberry pancakes I have ever had. The afternoon was a massage in the hotel spa (praise him) and then happy┬á┬áhour in the rooftop bar which is super cool. They also offer an open air bar in the summer months, which I kindly passed on in the 3 degree weather, but also looked houseWhen we did finally venture out for dinner, the comfort of Chicago deep dish pizza was the only route to go and naturally we chose the best deep dish around at Pequod’s. If you like spicy food, I suggest going with the Giardiniera option which is just a spicier sauce and added jalepenos. Also, something to consider when ordering is that I could only eat one piece after a little salad and a breadstick because it’s so filling. Each slice is large and obviously deep dish so it’s a lot of food. Last added note, if you like to stay local, try 312 Goose Island┬áBeer Co. on tap. It’s brewed right up the street.

Day Three:

Brunch at Southport Grocery. Epic. Nuff Said. Bread pudding pancakes, their signature hash, chorizo and eggs which mimics chilaquiles and brisket and gravy. Yeah, just so good and most of the items are available to shop grocery style as well. It’s a small place so plan on a little wait. There is a coffee shop across the street to grab a cup while you wait.

Once our bellies where full we decided to do a little walking so we ubered to Wicker Park to walk around Milwaukee Ave.

These were my favorite spots:

The Robey Hotel: As I said above, I am in love with the London House, but I did also visit a really cool new hotel in the five points area of Wicker Park that might give the London House a run for it’s money. It’s a smaller boutique hotel, with only 14 floors, but seriously cool vibes. I felt like I was in a Rolling Stone shoot the entire time we were there. Apparently the building was an old abandon spot that they turned into a really rad hotel. I didn’t see the rooms, but judging by the rest of the hotel, they are probably filled with cool decor and vibes.hotel robey 1hotel robey 2hotel robey 3

David’s Tea– tons of tea options to take to go or drink on the spot. They also had really cool, updated ways of making tea at home in a pot or just one cup.

Mojo Spa– all locally made and natural bath salts, scrubs, makeup, candles, etc. Amazing smells. Try the candle moisturizer. You literally burn the candle and the wax becomes a moisturizer. Pretty cool. Once you decide what you want, they make it for you in shop.

U.S. #1 vintage shop– a few doors down from Mojo Spa is what is now my favorite vintage spot in Chicago. Walls of boots and racks of coats cover the store. I personally bought a cheetah faux fur jacket from the 50’s that I die for and some zebra patterned faux fur boots that are aggressive and awesome.

Once we left Wicker Park, we cabbed over to Michigan Ave, because you just kind of have to. These are the more high end spots, but there is also a huge Topshop and Zara right on the corner that you shouldn’t miss.michigan aveDay three was jam packed. Following shopping, we got ready for our night at the Chicago Bull’s game. Before the game, we grabbed tacos at this cool spot near the arena called Federales. It you are a tequila drinker, order an ice glass tequila shot. Once you take your shot, you can throw your glass against this large bell and try to hit it. Sounds simple, but it’s actually really fun. The tacos are also really great.chicago bulls gameOn to the Bull’s game, where the Bull’s came back after being down 18 points to win. Needless to say, it was an exciting night. For ticket’s we bought on Craigslist, which worked really well for us. We found a guy wanting to sell out his suite that night (which is sort of against the rules, but whatevs). We got a great deal on the tickets ($100/ticket) and also got to live that suite life. Whoop!

Day Four:

Since day three was so full, day four was a little more chill. Most of the day was spent catching up on emails and hitting the gym. My boyfriend used to live in Chicago, so we finished our night by catching a service at his old church, City Church. If you are into church, I highly recommend it. There is an open door policy, chill vibes and honesty. I really enjoyed it.

My Chicago wardrobe is linked below. Click the pics to shop!

Email me at [email protected] if you have any Chicago questions or if you visit any of these places! Would love to hear your feedback.




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  1. Thanks for all of this! We moved here 2 years ago, Logan Square, which is not far from the new Robie Hotel, which I love!

    I have been to Mojo (obsessed with their shave bar) and am excited to go down the street to US #1 Vintage Shop!!

    As for tacos we usually go to ‘BIG STAR’ or
    ANTIQUE TACO but I will totally try your recommendation at least to be able to toss a tequila glass ­čÖé

    Happy travels and come back soon!

    1. Yes! You have to check out that vintage store! It’s amazing!
      And who doesn’t love to throw an ice glass?!?!

  2. Wow! I want to go to Chicago now! Thanks for all the great info on the city. I am always excited to see what you did, where you went, and what awesomeness you wore. That was a fun adventure. Great Blog!

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