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A skyline marked by iconic skyscrapers and neighborhoods each with their own character — Chicago quickly became the city I waited too long to visit.

A short 72 hours in the Windy City revealed the extensive amount of experiences, foods to try, and places to see in the city. Just three days barely scratched the surface as to what can be experienced. From taking to new heights at places like the Skydeck, to intimate corners in quaint coffee shops, checkout this first-timer’s weekend guide to Chicago.

The First-Timer’s Weekend Guide to Chicago

How to get to Chicago

  • With choices of O’Hare or Midway Airport, direct flights from major US hubs are readily available. If arriving into O’Hare, the blue line on the CTA train is easily accessible inside the airport for a direct route into the heart of Chicago (average 45-60 minutes).

Where to stay in Chicago

  •  Waldorf Astoria Chicago: City luxury is redefined in this beautiful hotel in the Gold Coast neighborhood. Central to most sights, the hotel exists as a retreat with high-touch service and amenities. Read the Waldorf Astoria Chicago Review.
  •  The Blackstone, a Renaissance Hotel: A classic Michigan Avenue hotel, and an icon, the hotel combines Beaux-Arts architecture and luxury. The hotel’s views over Michigan Lake and location in the heart of downtown make it a classic Chicago experience. Read the Blackstone, a Renaissance Hotel Review. 

The Waldorf Astoria Chicago The Waldorf Astoria Chicago

Where to eat and drink coffee in Chicago

The options are endless, with classic establishments and new moves in forward thinking restaurants. Here are a few to try during a weekend in Chicago:

  •  Bernie’s Lunch and Supper: A newer establishment in River North that pairs a beautiful space with Mediterranean influenced dishes. Inspired and created by Chef Ryan Sand, the menu showcases a cuisine marked by homey dishes filled with fresh ingredients.
  •  Cindy’s at Chicago Athletic Association: This rooftop dream of a room is a happening spot for sunset drinks and shareable platters with a view.
  •  The Allis at Soho House: A perfect spot for a tasty breakfast, with classics like soft boiled eggs with soldiers.
  •  Sociale: Late night eats, and small plates inspired by global cuisine.
  •  Avec: Minimalism paired with inventive dishes, has marked this restaurant as a “don’t miss” while in Chicago.
  •  Beatrix: Healthy options like avocado toast, and pressed juices.
  •  Doughnut Vault: A cute spot for tasty fresh doughnuts — note: once sold out, bakery closes!
  • Get Caffeinated at: Intelligentsia, Asado Coffee, & Bow Truss Roasters.

What to experience in Chicago

  •  Helicopter tour: I couldn’t recommend this one more than anything experienced while in Chicago. A sunset tour was magical, and gave a different point of view over the city that was truly second to none.
  •  Chicago CityPASS: This will be your saving grace on a busy weekend, plus massive benefits for the purchase. It gives you VIP entry to Shedd Aquarium, fast pass to Skydeck, VIP entry to Field Museum,  entry too Museum of Science and Industry with VIP entry or 360 Chicago Express entry, and VIP entry to Adler Planetarium or fast pass to Art Institute of Chicago. During the busy season, these experiences are impacted with long lines, so having a fast pass or express entry will optimize your time.
  •  Best view: 360 Chicago was the highlight for a view over the city.
  •  Most enjoyed museum: Art Institute for it’s extensive collection of Impressionist art and multiple rotating exhibits.
  • Experience Millennium Park: You’ll find highlights like the bean, free concerts and more in this great area to walk around and enjoy.
  •  Architecture tour by boat: A good introduction to the multiple buildings and history behind Chicago’s skyline.

Bon Traveler’s Tips

  •  CityPASS is a great add-on for ease and savings.
  •  Take advantage of the extensive public transportation with a CTA pass.
  •  Mind the weather, and come late spring through the fall for best temperatures.

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*I was welcomed as a guest of Chicago Tourism. As always all opinions are own.

PS — Are You Booking a Trip Soon? Use My Booking Checklist!

These are the sites I use most to book my own trips. Using the links below is a great way to support Bon Traveler’s travel journalism at no extra cost to you. If you need help organizing your itinerary, get my free travel itinerary template here.

1. Book Your Flights

I use Skyscanner to find the best flights. It searches 100s of airlines and websites across the globe to ensure you’re not missing out on any route options or deals.

2. Book Your Accommodations

I use for hotels and guest houses. They have the biggest inventory and consistently offer the best rates.

3. Book Your Tours & Experiences

I use Viator or Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check both as their inventory varies depending on the destination.

4. Book Your Rental Car

Self-driving is the best way to explore most destinations. I use Discover Cars for our rental cars, select full coverage insurance, and opt for a reputable company like Alamo, Hertz, or Sixt.

5. Don’t Forget Airport Lounge Access

I use Priority Pass to gain access to 1,400+ VIP lounges and airport experiences worldwide. The Priority Pass app is the first thing I check when I have a layover. I’ve been a member for over a decade, and having a comfortable place to relax before and between flights makes air travel so much more enjoyable.

6. Don’t Forget Travel Insurance

I never leave the country without travel insurance. It provides comprehensive protection in case anything goes wrong (ie. illness, injury, theft, and cancelations, etc.). I use it frequently for my travels to stay protected.

My favorite companies that offer the best coverage and rates are:



  1. After New York I have always thought, the next travel I will go to Chicago!Your photographs are amazing, also your blog, is so clean, tidy, and simple to see. You have a new follower! I’m a graphic designer and amateur photographer, and I love travelling and take a million of shots!

    • Jessica Wright Reply

      Ah thank you so much Luana for the kind words and support!

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