Fashion Lifestyle Travel

Chicago Travel Guide – Weekend Trip

November 7, 2019

Welcome to my Chicago Travel Guide! Brrrr… just got back from a very cold and quick weekend trip in Chicago. First impression = food and architecture. I wish I had maybe another day or two to try out all the restaurants and see more parts of the city. Here’s a quick guide on what to pack, where to stay, what to do, and where to eat!

What I Packed for Chicago

Where to Stay in Chicago

  • LondonHouse Chicago – The interior, room decor, service, and views were amazing. I highly recommend it. It’s centrally located in the heart of downtown with views of the Chicago Riverwalk and vibrant turquoise water, so you’re walking distance to everything!

What to Do in Chicago

  • Chicago Bean in Millennium Park – Super cool sculpture in the shape of a bean! Try to go as early as possible to beat the crowds.
  • Skydeck Chicago – Approximately 1.5 million tourists visit this every year! For $24 and an hour wait, you’ll be taken up to 103 floors to see breathtaking views and take pics in a clear glass box. Because there is so much people, you only get about 60 seconds in the Skydeck box to take a few pics. After that, you can stroll around the floor and see views from other angles.
  • Chicago Theater – Very cool during the day, but even better at night!
  • Coffee Alley Way – Super IG worthy and unfortunately the coffee shop was closed when we got there, but it was such a cute alley.
  • Lincoln Park Zoo and Honeycomb – Get dropped off at the Lincoln Park Zoo, the zoo is free and open to the public. I got to see zebras and camels which was really cool. From the zoo, you’ll see a beautiful Chicago landmark called the Honeycomb that is really cool! Perfect for photos plus it frames the entire city.

Where to Eat in Chicago

  • Pequod’s Pizzeria – It wouldn’t be Chicago if you didn’t try their deep dish pizza! We got the small size and added cheese, pepperoni, and sausage to keep it simple. The other popular option was Lou Malnati’s Pizzeria but we didn’t have enough time to go there.
  • Bavette’s Bar & Boeuf – One of the best steakhouses I’ve been to. I’m a huge ribeye fan but I ended up trying the petite filet mignon instead along with mac & cheese. It was perfect. The wait was 4 hours BUT here’s a pro tip! There’s an open bar seating area that serves their full menu, so order a drink and hover around people until they leave! You have no choice but to be aggressive.
  • Au Cheval – They’re known for their Au Cheval burger with a fried egg plus a thick-cut juicy bacon. Also order the Foie Gras and Scrambled Eggs and you will NOT be disappointed!
  • Ramen-San – I like to try ramen at different cities, and this one was pretty good. The broth was thick and the pork belly was pretty tender.
  • Other places I wanted to try but didn’t have enough time: Lou Malnati’s Pizzeria, The Purple Pig, Girl & the Goat
jenny tran chicago londonhouse hotel
Chicago LondonHouse Hotel
jenny tran chicago skydeck views
Chicago Skydeck – 103 floors
jenny tran chicago millennium park bean
Chicago Millennium Park – Bean
Chicago Coffee Alley
Chicago City Views


  • Reply
    November 8, 2019 at 11:43 am

    Love all these tips and the photos came out amazing

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