A Quick Guide to the Best of Chicago, Illinois

Destinations

Jun 15

After visiting Chicago, USA many times, here’s my ultimate bucket list of travel ideas for the Windy City. Whether your trip is a two-day weekend in Chicago or a full week, here are the best trip ideas in one quick travel guide. The prettiest places…

When a friend recently asked for my Chicago recommendations, I realized that for all my visits there over the years, I’d never written a proper city guide! Today, we’ll remedy that - I’ve pulled out all my tried-and-true favorite places and newer spots on my radar to give you a quick travel guide to the best of Chicago, Illinois.

Where to Stay in Chicago

Chicago is full of great (and not-so-great) hotels, a bit of review sleuthing can tell you which type you’re looking at. That said, the Waldorf Astoria in Chicago feels almost like Paris, and the bathtubs are glorious, so it tops my list!

For something that’s a bit cooler, more modern, and certainly more economical, check into The Freehand Chicago. Their hotels and restaurants always have such a relaxed-yet-thoughtful vibe - and good food.

What to Do in Chicago

The Art Institute of Chicago is always a must-visit for me - any chance to see Degas’ Little Dancer! Nearby, the (free) Chicago Cultural Center is home to an incredible Tiffany dome ceiling that’s definitely worth a stop.

When the weather’s nice, an architectural river cruise is a wonderful way to get to know the city - plan this for the beginning of your trip if you can!

No trip to Chicago is complete without shopping at P.O.S.H. - it’s a wonderful mix of vintage and new items, curated by the shop’s charming owner, Karl. He travels to Paris to source vintage finds, and I’m always leaving extra space in my luggage to bring them home. Did I mention there’s a little champagne bar just a couple of doors down?

If you’re visiting with a car in the spring or summer, Chicago’s Botanic Garden is a lovely stop just outside the city. During the holiday season, shop the Christkindlmarket - and catch the Joffrey Ballet’s classic production of The Nutcracker (it’s the absolute best in my book).

Where to Eat in Chicago

Breakfast & Brunch:

Blue Door Kitchen & Garden and The Allis at Soho House (they also do afternoon tea!) are my top picks. The local chain Yolk has a special place in my heart, and I’ll stop into any Dollop Coffee Co. when in need of a cappuccino. The Hampton Social is also a fun brunch spot - equal parts Instagram opportunity and good food.

Lunch & Dinner:

For something casual, head to Velvet Taco or have Chicago’s famous deep-dish pizza (my picks are Giordano’s or Gino’s). For a lingering sit-down meal, try the no-fail RL restaurant, Au Cheval (the burger!!), Margeaux Brasserie, or Maple & Ash. On my list for the future: 3 Arts Club Café, Ēma, Nonnina, and Bavette’s.

Drinks with a View:

The Signature Lounge at the 96th floor of the Hancock building is my all-time favorite - it’s more than worth the wait for a table by the window! The next best view is at London House’s rooftop bar - though Drumbar and Cindy’s are also great spots for a drink with a city view.

Sweets:

If you only get one sweet in Chicago, let it be from Doughnut Vault - quite possibly the best doughnuts ever. For something more Parisian, head to La Fournette, Toni Patisserie, or Alliance Bakery. Ooh, and the delicious Vosges Chocolates!