A Guide to Visiting Chicago in the Summer

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​Lauren Barrett

Welcome to Chi Town, The Windy City, and the Paris on the Prairie. That's right, today, we are discussing Chicago, Illinois' largest city and the third largest city in the U.S.

Situated on Lake Michigan, Chicago is known for its skyscrapers, museums, and deep dish pizza.

I've  been twice now. Once when I traveled with some friends after high school in 2007 to stay at my one friend's sister's place. We packed a lot in in a little bit of time, and I must say this is a place to go back to.

​My husband and I were supposed to go back for our 5th anniversary to see the Cubs, Whitesox, and Brewers all play, but COVID ruined that. Fingers crossed for next year. 

*Update* James and I were able to go to Chicago in July 2021 to visit all the baseball stadiums.

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1st Time Itinerary 

• Walked around the Chicago Botanic Garden
• Saw the Broadway play, Wicked, at the Nederlander (formerly known as the Oriental) Theater. 
• Saw the Cubs play at Wrigley Field.
• Ate a huge banana split at Margie's Candies. 
• Went up to the top of the John Hancock Building.
• Went to Millennium Park and took pictures in front of the Bean.
• Took a horse and carriage ride from Chicago Horse & Carriage.
• Walked on Michigan Avenue and the Magnificent Mile, Chicago's premier commercial district. 
• Had a fancy dinner at Nacional 27.
• Ate deep dish pizza. 

2nd Time Itinerary 

Logistics:

• Flew into Midway Airport and out of O'Hare Airport. 
• Stayed at an Airbnb near Horner Park
• Stayed 6 days, 5 nights
• Traveled mostly by the Brown Line Train (The "L) around the city

Things we did: 
Day 1

• Arrived at airport
• Lunch and drink at Forbidden Root Restaurant and Brewery
• White Sox game at Guaranteed Rate Field

Day 2

• Rented bikes at Chicago Bike and Roll near Millennium Park
• Rode along Lake Front Trail which is right along Lake Michigan
• Lunch and drinks at Caffe Olivia, which is right on the beach
• Dinner at an Italian restaurant, Siena Tavern, in downtown Chicago.

Day 3

• Took train to the Chicago River Walk and walked along the water and got ice cream. 
• Had a mishap with our rental car and then had to take an Uber to Milwaukee. 
• Went to the Brewers game at American Family Field in Milwaukee. 
• Spent the night in Milwaukee

Day 4

• Ubered back to Chicago
• Fancy dinner at Steak 48
• Walked to Navy Pier to the Beer Garden for live music and fireworks

Day 5

• Went to Wrigleyville to walk around and then went to the Cubs game at Wrigley Field
• Dinner from Pequod's Pizza

Day 6

• Brunch near Lincoln Park
• Walked around the North Pond in Lincoln Park
• Ice cream in the area
• Went to airport

*What I wished we could've done*

• Rent kayaks in the Chicago River
• Spend a day at one of the lake beaches
• Have more time to explore Milwaukee
• More time biking along the Lakefront Trail
• Visiting Lincoln Park Zoo

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My name is Lauren, and I was born in New Jersey, grew up in West Virginia, went to college in Pennsylvania, and now live and work in North Carolina. I'm a high school teacher of the deaf and hard-of-hearing by day, a cross country coach by the afternoon, a writer by night, and a full time mom to an amazing toddler. I love my faith, running, watching baseball, chocolate, scrapbooking, pretending I would actually do well on the Amazing Race, re-watching The Office, listening to Bobby Bones, and helping out all moms.

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