When a friend recently asked for my Chicago recommendations, I realized that despite numerous visits over the years, I had never prepared a formal city guide. Today, we’ll change that, as I’ve compiled a fast travel guide to the best of Chicago, Illinois, featuring both tried-and-true favorites and recent destinations on my radar.
Read Also: Round trip flights to Chicago
Where to stay in Chicago
Chicago has plenty of amazing (and not-so-great) hotels; a little review investigation will reveal which type you’re looking at. That being said, the Waldorf Astoria in Chicago seems almost like Paris, and the baths are stunning, so it tops my list!
The Freehand Chicago is a bit cooler, more modern, and probably less expensive. Their hotels and restaurants usually exude a comfortable yet thoughtful atmosphere, as well as delicious food.
What to Do in Chicago?
Any opportunity to visit Degas’ Little Dancer at the Art Institute of Chicago is something I always make time to do. The nearby (free) Chicago Cultural Center features an exquisite Tiffany dome ceiling that is well worth a visit.
When the weather is nice, an architectural river tour is a great way to get to know the city; plan it at the start of your trip if possible!
No trip to Chicago is complete without a stop at P.O.S.H., which offers a fantastic mix of old and new products chosen by the shop’s lovely owner, Karl. He flies to Paris to find vintage treasures, and I’m always leaving extra space in my luggage to bring them home. Did I mention there’s a small champagne bar just a few doors down?
If you’re visiting Chicago by vehicle in the spring or summer, the Botanic Garden is a beautiful stop just outside the city. During the Christmas season, visit the Christkindlmarket and see the Joffrey Ballet’s famous version of The Nutcracker (the greatest in my opinion).
Where to Eat in Chicago?
BREAKFAST & BRUNCH:
My preferred picks for breakfast and brunch are Blue Door Kitchen & Garden and The Allis at Soho House (which also serves afternoon tea). Yolk, a local chain, holds a special place in my heart, and I’ll stop into any Dollop Coffee Co. for a cappuccino. The Hampton Social is also a fantastic brunch spot, with equal parts Instagram opportunities and delicious food.
LUNCH & DINNER:
For a casual lunch or dinner, try Velvet Taco Giordano’s or Gino’s deep-dish pizza. For a longer sit-down lunch, try the tried-and-true RL eatery Au Cheval (the burger!!), Margeaux Brasserie, or Maple & Ash. My plans include visiting 3 Arts Club Café, Ēma, Nonnina, and Bavette’s.
DRINKS WITH A VIEW:
My personal favorite is the Signature Lounge on the 96th story of the Hancock building, which is well worth the wait for a table by the window. The second finest view is from London House’s rooftop bar, however, Drumbar and Cindy’s are also excellent places to have a drink with a city view.
SWEETS:
Doughnut Vault offers the greatest doughnuts in Chicago, making it a must-visit spot. For something more Parisian, visit La Fournette, Toni Patisserie, or Alliance Bakery. Oh, and those delectable Vosges Chocolates!
