First-timer’s advice: What to do in Chicago

It’s July. Doesn’t it feel like everyone is on vacation but you?? Maybe it’s just me. But it does seem like everyone I know is going to my home town of Chicago! I’ve given several people recommendations on their first trip to the Windy City. What are your favorite spots??


  • Hang out in Millennium Park – It’s the gathering spot for visitors and locals alike! You have the “bean,” free summer concerts, art exhibitions and great people watching!

cloud gate

  • Explore Navy Pier – Yes it’s touristy but worth checking out if you’ve never been! Wander around the shops, grab a beer at the beer garden or ride the ferris wheel.

one world trade center under cloudy sky during daytime

  • Take a cruise down the Chicago River – You can stroll down the Riverwalk but why not book an architecture cruise and see Chicago’s iconic buildings from a boat? (Tip: there’s usually deals on Groupon!)

river between trees and city skyscrapers

  • Swim in Lake Michigan – North Avenue Beach has an unbeatable skyline and volleyball buffs will love the sand courts.

north ave beach

  • Shop on Magnificent Mile – You don’t get this kind of concentrated shopping many other places. Michigan Avenue is lined up with endless amounts of restaurants and stores. Also worth a peek is the eight-story Water Tower Place mall.
  • Go to a Cubs game – Even if you’re not a baseball fan, the iconic Wrigley Field is worth a visit. Go early and grab a bite or a drink at one of the dozens of bars and restaurants in Wrigleyville.

wrigley field.jpg

  • Visit a Museum in Grant Park – This lake side park covers 319 acres is home to the Shedd Aquarium, the Adler Planetarium, the Field Museum and the Art Institute and the “Married with Children” fountain 🙂


The best place to see the city is from up high of course! There are plenty of rooftops and observatories open for the warm summer weather.

aerial photography of building city lights

  • Cindy’s Rooftop – Located at the Chicago Athletic Association, this restaurant and rooftop bar offer unparalleled views of Millennium Park.
  • The J Parker – This rooftop spot at Hotel Lincoln offers views of Lincoln Park.
  • 360 CHICAGO – The observation deck is located 1,000 feet above the Magnificent Mile in the John Hancock Building and gives you 360 degree views of city and lake. (Tip: save the $23 and spend it on drinks or a meal at the building’s restaurant The Signature Room. Same views, no admission fee!)


  • Chicago Hot Dog –  A Chicago Red Hot is an all-beef frankfurter on a poppy seed bun with onions, mustard, relish and a sport pepper. Gene and Jude’s has been around since 1946. They add french fries to their dog, but be warned: they don’t serve ketchup! And the McDonald’s next door caught on and now charges for ketchup packets.


  • Deep Dish Pizza – Cheese on bottom, sauce on top, that’s how it goes. Check out Pequods, Lou Malnati’s or Chicago Pizza and Oven Grinder Company.
  • Italian Beef Sandwich – This is quintessential and Chicagoans take it very seriously! Sweet peppers or giardiniera? Cheese or no cheese? However you order it, you can’t go wrong. There’s Luke’s, Tony’s, Al’s or Portillo’s to name just a few. (Tip: Order it wet and they dip the whole sandwich in au jus).
  • GLUTEN FREE FRIENDS: There are a only a handful of options when it comes to these three iconic dishes! You can find GF deep dish at Chicago’s Pizza. Buona Beef has a GF beef, but definitely not a safe kitchen for Celiacs. And I’m still looking for a Chicago Dog!


  • Intelligentsia Coffee – trendy coffee shop that started in Chicago
  • The Green Mile Cocktail Lounge – former mob hangout keeping the authenticity of a 40s jazz club
  • The Aviary – upscale ambience with crazy instagrammable drinks
  • Emporium – a barcade with multiple locations
  • Three Dots and a Dash –  a cool underground tiki bar (Tip: Go for happy hour when you don’t need a reservation!)


three dots and a dash


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