Itinerary: One Perfect Day in Chicago

Jessica Peterson


The Windy City is the third largest and definitely one of the most expensive cities in the U.S. but you’ve got to experience it at least once. If you like architecture, shopping, food, and music, you won’t be disappointed. Chitown is a walking city if you’re staying in the right place and know where to go. Follow this itinerary for one perfect day in Chicago…

Park Hyatt Chicago


I like to start the day at any hotel by throwing open the curtains. You can’t do that at Park Hyatt Chicago. Instead, you push a button to raise the blinds and are presented with a stunning view of the Chicago Water Tower, surrounding architecture, and a swath of Lake Michigan. It’s tempting to stay in the soaking tub all morning, but Park Hyatt Chicago is the way to experience The Magnificent Mile, Chicago’s famous shopping district. Head out on foot and get your start on Michigan Avenue.



This cafe on steroids is a full sensory experience. Two floors of gastronomical happiness are promised in this modern take on an ancient concept — the Italian deli. Start with a cappuccino at the cafe and work your way upstairs to ogle the cured meats, gazillions of cheeses, handmade pastas, and extensive wine collection. Sit down for a wine tasting while munching on some anti-pasto at La Piazza. Then make your way to the pizza, pasta, or seafood stations and indulge some more. Roll yourself downstairs for a gelato or even pick up some gifts. Eataly is pricy but totally worth the experience.

The Magnificent Mile


Stroll the clean and manicured Magnificent Mile to shop or window shop everything from the Apple store to Nordstrom Rack. Street musicians and performers will keep you entertained. See the shopping and dining map.

Cafe Iberico


I’ve been to Barcelona and Cafe Iberico easily rivals restaurants in the motherland. What looks like a tiny cafe is actually a spacious multi-room restaurant serving quite large tapas. Sit at the bar to order drinks and tapas as a respite to your shopping spree on The Magnificent Mile. You won’t be disappointed ordering the Pulpo a la Gallega — seared octopus grilled to perfection on a bed of crispy potatoes. If you’ve never tried octopus, this is a great introduction and not too weird even for the novice. You will also need a plate of Salmon Alhumado, classic smoked meat topped with capers and fresh dill cream.

Lincoln Hall


Lincoln Hall is an intimate concert hall and the perfect place to catch an indie band on a weeknight. Like many Chicago buildings, Lincoln Hall has a storied past, having been used as a nickelodeon, garage, machine shop, cinema, and even an FBI outpost to catch ’30s gangster John Dillinger. Ellie Goulding, Foster the People, and Tame Impala have performed there. I was there to catch YouTube darlings, Pomplamoose and had a great view from the stairs. Only street parking is available, so get there early to avoid circling the block for an hour.

Pizzeria Uno


I grew up on Uno’s pizza. It was a staple in my childhood. My dad took me there what seems like every week. We always ordered the same thing — mozzarella tomato deep dish with extra tomatoes and a house salad. Uno’s still has the best pizza crust I’ve ever tasted. It’s flaky, buttery perfection. My Chicago-native friend urged me to try Lou Malnati’s and I did. Perhaps its the nostalgia, but I still love Uno’s most. The interior is tiny and cramped but has all the charm of its 1940’s roots. Wind up your day with gooey mozzarella stuck to your chin. I guarantee you’ll sleep well.

What are your favorite spots in Chicago?

Jessica Peterson
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Jessica Peterson

Jessica Peterson is a travel filmmaker, photographer, and journalist. She released her first documentary film about indigenous culture on Guam in 2016, after having lived nearly 7 years on the Pacific island. Jessica is currently on the Great American Roadtrip in her Airstream trailer.
Jessica Peterson
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  • Wow! What a great day in Chicago! That pasta in the window….holy cow. My favorite thing to do in the city is to catch an improv show at Second City.

    Thanks for the share! Now you have me wanting to pay Chicago another visit. You also have me hungry for pizza.

    xx Hailey

    • Thanks for reading, Hailey. P.S. I’m always hungry for deep dish pizza!