Planning your first day in Chicago

Planning your first day in Chicago

July 22, 2015

If you’re planning a trip to Chicago, but you don’t know where to begin, then we have a great starting point for you.

What about starting off with a bang by jam-packing day #1 in the city with tons of Chicago-unique adventures?

Chicago has SO much to offer, and has something for everyone. From exceptional theatre and museums to unreal sporting events – it is a little overwhelming as to where to start. Not sure if you want to do more of a history-based trip, a shopping-based trip, an arts-based trip…or if you want to chase all the sporting teams of this big city? Well then, dip your toes into everything on the first day before deciding where to focus the rest of your visit.

This guide is a great tool to help you ground your feet in the Windy City.


1. Yoga in the Park

(8:00 am – 8:45)

Start the day off right by attending one of the free yoga sessions offered in Millennium Park every Saturday on the Great Lawn. Not visiting on a weekend? Not to worry – classes run Wednesday mornings as well.

Classes run from 7 am through to 11 am and are  45 minutes each. Yoga in the Park features Tai Chi Classes, Zumba, Pilates, and general Yoga.



2. Picnic and Tour of Millennium Park

(8:45 – 10:15)

Millennium Park is an iconic Chicago park located in the centre of the downtown business district. This park was transformed from an industrial wasteland into a world-renown tourist attraction.

Already in the park from your early morning yoga session, head over to the Chase Promenade and set up a picnic on the Running Table. This 100′ long picnic table is made of only recyclable materials, and the location could not be better for your breakfast with a view.


After breakfast, explore the park’s several attractions including the Jay Pritzker Pavillon, the Cloud Gate (Featuring Chicago’s infamous BEAN), the Crown Fountain, the Lurie Garden, the Wrigley Square and Millennium Monument, the Boeing Galleries, the BP Bridge, the Harris Theatre, the Exelon Pavilions, and the Nichols Bridgeway

Find a map of the park here

To see if there are any featured exhibitions taking place during your stay, check out this link here. 


3. The Art Institute Of Chicago

(10:15 – 10:30)

Stop in at the Art institute of Chicago and take a quick peak. You won’t have time to see the exhibits today, but grab a brochure to come back during the rest of your stay. Or, if you only have one day, swap out shopping along the magnificent mile, or lunch at Portillo’s for this renown display.



4. The Magnificent Mile 

(10:30- 12:00)

Take a Walk down Michigan Ave for the best shopping in the city. This strip of stores is known for its wide variety of boutiques and stores to satisfy any shopper. This unbeatable selection of stores will get everybody doing some window shopping, or real shopping for that matter. Stop in at the Water Tower Place on Michigan Ave to continue your shopping.


After exploring the Magnificent Mile, head north on Michigan Ave. Venture over the bridge and turn left on Ontario Street.




5. Italian Beef at Portillo’s

(12:00- 1:00)

This retro chain serves chicago-style hot dogs and is an experience you need to have before leaving the city. After chowing down on your dog, head east towards the waterfront.




6. Navy Pier

(1:00 – 2:30)

Chicago’s Navy Pier is about a half hour walk from Portillo’s, and the perfect way to walk off your heavy lunch. The pier is Chicago’s number one tourist attraction and the top-visited leisure destination  in the Midwest.

It is packed with loads to do. Ride the ferris wheel for a view of the city, explore the indoor crystal gardens, try out the Amazing Chicago Funhouse Maze, Shop for the best Chicago souvenirs, and gather information about their boat tours – because hey, you might just come back tomorrow.

Find more information about the Chicago Navy Pier here




7. Lakeshore Drive Bikeride

(2:30 – 3:15)

Hop on a divvy bike outside of the navy pier and start your bike ride north along the lakefront path. This path is loaded with bikers, runners, walkers, rollerbladers, and skateboarders – and you can who all experience the beautiful view of lake Michigan together.


Switch your divvy bike at Oak Street Beach – but first stop for a quick refreshment and a dip in the water before continuing your bike ride.




8. North Avenue Beach Volleyball

(3:15- 4:30)

Stop at North Avenue Beach for a game of Beach Volleyball.



9. Wriggleyville

(4:30 – 6:30)

Grab another Divvy and head north-west to Wriggleyville, pass the Diversey harbor and the Belmont Harbor on your way for another scenic view.

Wriggleyville is the heart of Chicago’s sporting community. This upbeat neighborhood is worth checking out. Take a pitstop at the Cubs stadium to grab tickets for the next upcoming game while you are in town. Purchase some cubs memorabilia and experience the festivities of post-game fun.




10. Deep Dish Pizza

(6:30 – 8:30)

Giordano’s is located in the centre of buzzing Wriggleyville. Experience Deep Dish Pizza at one of Chicago’s specialty pizza parlors.





11. Ride the L back to the city

Take the L back to the city.





12. Dessert at the John Hancock Tower

Stop at the John Hancock tower for dessert and an absolutely outstanding view of the city before heading back to your hotel.





Get ready for day #2


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