Chicago has a population of 2.7 million people. There is so much to do and see and it can easily get overwhelming when choosing what to fit into your itinerary. Check out my post on the perfect itinerary for a three-day visit to the Windy City. If you’re still torn between where to spend your time, read along for what to do and what to skip (and why!).

Explorer Pass vs. City Pass

These passes are essentially bundled, less expensive packages of attractions that you can purchase ahead of time rather than buying tickets individually at each attraction. With the Explorer Pass you can choose a set of 3 or 5 activities (out of 25) you’d like to do. City Pass offers 5 fixed attractions, however, this pass gets you ahead of all the lines. If you go in an off season, the flexibility of the Explorer Go Pass may sound attractive. But if you go during peak season (say, Fourth of July weekend) expect the lines to attractions to be much longer and therefore the City Pass is the way to go!

Skydeck vs. 360 Chicago

360 Chicago is located in the John Hancock Observatory where you can see 360 degree views of the city. The newest attraction Tilt! offers guest the opportunity to view the city from a glass wall that tilts 10-30 degrees and they also offer yoga classes on Saturday mornings (both for additional fees). My suggestion is head to the Signature Lounge at 96th instead. You’ll spend about the same but skip the lines and get a drink in return! The Sky Deck, located at the Willis (aka Sears) Tower also features great views and the thrill of stepping on a glass box that you can see straight down 1500 feet. If you go at sunset, you will get amazing views of the city!

Architecture Boat Tour vs. Big Bus Tour

The Architecture Boat Tour is one of the best attractions loved by visitors and locals alike. It’s a great way to view the city and learn about its rich history. The bus tour is lengthy and slow. Skip the bus tour and go for the boat tour instead.

Magnificent Mile vs. Other Neighborhoods

Michigan Avenue (aka Magnificent Mile) boast designer shops the likes of Chanel and Yves Saint Laurent and many well-known stores such H&M. But unless you’re craving some major designer threads, head to Wicker Park and Bucktown for boutiques and shops with unique items and great souvenirs! We stayed in the Gold Coast which also has some great shopping! You’ll likely stroll through the Maginificent Mile at some point getting to other attractions and you can always window shop as you walk by!

Deep Dish Pizza vs. Chef-Driven Eats

A visit to Chicago is not complete without a slice or 3 of its famous deep dish pizza. If you absolutely have to choose, this is the best choice. If you, like me, eat more than one meal a day, opt for the chef restaurants also. Girl and the Goat is awesome but be sure to make a reservation!

Navy Pier vs. Millenium Park

Although both spots are tourist-packed attractions, the Cloud Gate at Millennium Park is the one to choose. It is a great spot for pictures and a stroll through the park. You can walk over to the iconic Chicago Theater from here, too. The Navy Pier might be a better attraction if you’re bringing little ones since it has a small amusement park.