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Chicago Itinerary

How long was your stay?

6 Days

How did you travel?


Tell us why you traveled to this destination.

Chicago is one of my favorite places in the world that I try to visit as often as possible. On top of that, my best friends live there, so that is always a good excuse for a visit.

What was your itinerary?

Day 1: Went to Beatnik on the River and Garfield Park Conservatory.
Day 2: Architecture Tour, had lunch at Café Istanbul.
Day 3: Visited Prince Exhibit, Ohio Street Beach, Replay Lincoln Park.
Day 4: Explored Oak Street Beach, Play at Nederlander Theatre, Three Dots and a Dash.
Day 5: Enjoyed Cubs Game at Wrigley Field, Dinner at Eli’s Ark.
Day 6: Travelled Pizzeria Portofino.

Give us all the details! Tell us where you went and what you did on your trip.

Day 1: Already being familiar with Chicago, I knew exactly where to go when I landed. Goddess and the Baker is my favorite breakfast spot where I alternate between a matcha or a seasonal coffee and chose from their cartoonish sugar cookies. I sat along the Chicago River while I ate my breakfast. When lunchtime came around, I headed to Beatnik on the River, a swanky restaurant where you can watch the river roll by. Knowing I had a full week of eating indulgently ahead of me, I chose a Fattoush salad and a coconut coffee mocktail. I spent time walking and shopping around the Fulton-Market area and then returned to River North, one of my favorite neighborhoods, to my hotel.
Next I met up with a friend at Garfield Park Conservatory, a botanical garden housing a myriad of plants in full bloom. For dinner, we headed to Handlebar, where the vegetarian nachos are not to be missed. We ended the night at one of my absolute favorite Chicago spots, Eli’s Ark, where they serve gelato decorated like animals.

Day 2: Day 2 began at Goddess and the Baker before I set out for one of my favorite activities in the city. The Chicago Architecture Foundation Center River Cruise provides an amazing way to observe the unparalleled architecture lining the Chicago River. During an hour and a half cruise, a knowledgeable docent explains the nuances of the cityscape. I have taken the tour more than once and never regret it.
I stopped for lunch at Café Istanbul for a Mediterranean salad. I met up with a friend for dinner at the Chicago Diner, one of my favorite stops for vegetarian and vegan comfort food. To finish off a day of eating well, we stopped at Niko’s Italian Ice for a cup to eat in the park nearby.
Day 3: After yet again returning to my favorite breakfast spot, I took in the excitement of River North, bustling with shops and restaurants. While I visited, I found an exhibit dedicated to one of my favorite musicians, Prince. Prince: The Immersive Experience explores his life and impact on the music industry. I grabbed a personal deep-dish pizza from Giordano’s. Though I initially had mixed feelings about the idea of deep-dish pizza, Giordano’s changed my mind.
I next strolled to Ohio Street Beach, a free beach relaxing enough to spend a whole afternoon. For dinner, I met up with my friend at Kitchen 17, a tasty vegan spot. Afterwards we went to Replay Lincoln Park, an extremely fun arcade style bar with a game to entertain everyone.

Day 4: I started my day at Oak Street Beach, where I had my morning ritual matcha and sugar cookie from Goddess and the Baker. I walked around the Gold Coast, a calm neighborhood for upscale shopping. I took in a matinee of a musical at the James M. Nederlander Theatre.
My friend met me for dinner at Nonnina’s for pasta. We stopped for milkshakes at Jojo’s Shake Bar, which serves a vast selection of shake flavors. We ended the night at Three Dots and a Dash, an upbeat tiki bar tucked into an alley in River North. Drinks are served in colorful, retro glasses. They also serve mocktails depending on your drink preferences.
Day 5: A friend and I met at Drink Happy Thoughts, a hole-in-the-wall coffee shop where you can drink your latte from a bear-shaped container. We next took in a baseball game at Wrigley Field, home of the Chicago Cubs. I may know virtually nothing about any sport, but I do know that a good time is guaranteed at this stadium.
For dinner and dessert, we headed back to those tried and true favorites of mine – the Chicago Diner and Eli’s Ark. Since it was my last night in Chicago, I indulged with grabbing a decadent ice cream taco from Parlor Pizza on my way back to the hotel.
Day 6: After a flight delay, I decided to grab one last breakfast from Goddess and the Baker, knowing I would miss it terribly after I left. I got fresh air walking by the river and then went to Pizzeria Portofino, for a delicious lunch of truffle fries and pasta.

Would you recommend this trip to a friend?


What was the highlight of your trip?

Each restaurant I went to was phenomenal. Though I’ve done both before, I really enjoyed the river cruise tour and going to a game at Wrigley Field. Replay Lincoln Park was also an unexpected blast!

If you were to take this trip again, is there anything you would add or do differently?

Chicago has an endless supply of entertaining places to go, so it’s tough to be disappointed here. That being said, I would skip returning to the Nederlander Theatre since more than one staff member was unnecessarily rude there.

@lizanthemum – (insta)

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