Chicago is a beautiful city that comes to life in the summer. If you are traveling to Chicago and want to make the most of your trip, here is my three day itinerary.
Quick Links
Where to Stay
Baseball at Wrigley Field
Deep Dish Pizza
Millennium Park
The Art Institute of Chicago
Grant Park
Girl and the Goat
Architecture Boat Tour
Bike the Lakefront Trail
The Purple Pig
Final Thoughts
Where to Stay
I recommend staying in either River North or Magnificent Mile. Both of these neighborhoods are north of the river and near many of the main attractions. The L is Chicago’s metro/ train system and can get you just about anywhere.
Day 1 in Chicago
See a Cubs Game at Wrigley Field
Going to a Cubs game at Wrigley Field can be an all day event to get the full experience. The stadium is in Wrigleyville which is easy to get to using public transportation. Join the fans for a pregame at one of the bars near the stadium. I enjoyed a beer on the rooftop patio of the Sports Corner Bar and Grill.
Once you’ve enjoyed a beer or two, make the short trek to the stadium and find your seats. My favorite part of attending a baseball game is all the food and drinks, and if there’s one stadium to get a hotdog, it’s Wrigley.
After the game, if you still have it in you, keep exploring the lively sports bars and pubs in the area.
Get Deep Dish Pizza for Dinner
For dinner, try some of Chicago’s famous deep dish pizza. There are a lot of options: Pequod’s is a local favorite, Lou Malnati’s and Giordanos are popular options, and Pizzeria Uno and Gino’s East are also great choices. Of those I have tried Lou Malnati’s and Gino’s East, and thought both were great. Next time I plan to try Pequod’s.
Day 2 in Chicago
Explore Millennium Park
Millennium Park is a 25 acre park south of the river and makes up the northwestern corner of Grant Park. Within Millennium Park is ‘The Bean’ which is actually named Cloud Gate. I thought the sculpture would be overhyped, but it’s actually really neat the way the skyline reflects off it.
If it’s a particularly hot day, cool off in the Crown Fountain just south of the bean. Even if you don’t want to get wet, the fountain has cool art installations worth checking out.
Also in Millennium Park is the Jay Pritzker Pavilion which holds various events and has a large lawn. In the summer there are frequent concerts in the pavilion, so check the events schedule ahead of time.
Art Institute of Chicago
The Art Institute of Chicago is a museum within Grant Park, and is one of the oldest museums in the US. Some of the most famous pieces in the museum are Seurat’s ‘A Sunday on La Grande Jatte’ and Wood’s ‘American Gothic’.
The museum is closed on Tuesdays and Wednesdays, so be sure to plan around that. Tickets are $25 per person and can be purchased ahead of time.
Walk around Grant Park
Grant Park is the huge park south of the river and along the lakeshore. Within it are Millenium Park, museums, Buckingham Fountain, and various sports fields. The park is home to many large events such as Lollapalooza and Taste of Chicago.
Check for events that might be going on in Grant Park while you’re there, in 2017 I stumbled upon Taste of Chicago which was awesome!
Get Dinner at Girl & the Goat and Drinks at Three Dots and a Dash
Girl and the Goat is a very popular restaurant in Chicago and therefore you need a reservation far in advance. After dinner check out the popular tiki bar Three Dots and a Dash.
Day 3 in Chicago
Architecture Boat Tour
Chicago is famous for it’s architecture and one of the coolest ways to see it is from a boat along the river. There are multiple companies that offer architecture boat cruises such as Chicago’s First Lady, Wendella, and Shoreline Sightseeing. The tours tend to be 90 minutes long and all start near the DuSable Bridge. The prices vary from about $35 to $50.
If you opt for the day time tour, remember sunscreen and a hat!
Bike Along the Lakefront Trail
Chicago has 18 miles of lakefront trail where you can walk, bike, or skate. I recommend grabbing one of the city bikes (Divvy) near Navy Pier and riding north along Lake Michigan. Whenever you want a break, find a bike dock and hang out at one of Chicago’s sandy beaches.
Get Dinner at the Purple Pig
Whenever I’m in Chicago, eating at the Purple Pig is a must! The menu is Mediterranean inspired with lots of pork and seafood options. Funny enough, my favorite thing to get is the grilled broccoli, it is delicious!
More Eats and Nightlife
Some other ideas for food are Portillo’s for hot dogs, Al’s for beef sandwiches, Eddie’s All Day Cafe and Bar, and Athena’s Greek Restaurant.
Other suggestions for nightlife are Utopian Tailgate, Cindys, Goose Island Taproom, and comedy at The Second City.
Final Thoughts
I think Chicago is a lot of fun to visit for those who enjoy the city life and appreciate food, culture, and art. I prefer to visit in the warmer months to properly enjoy Lake Michigan and the river.
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