Chicago is an incredible city any time of the year and at any hour. There's always something going on, friendly people to meet, and something delicious to eat. But like any other large city, tourists are often quickly overwhelmed and struggle to navigate the scene properly. On your next trip to Chicago, you'll be better prepared if you keep these tips in mind:
Don't stay right downtown
The concept of staying downtown can be misleading when it comes to Chicago. Downtown might imply being in the center of it all, but the area we refer to as the "Loop" is filled with nothing more than 9-5'ers and a few theaters. Staying right in the loop, you'll find yourself a bit farther from the action than you'd really like to be.
Instead, consider booking a stay in the trendy River North or Streeterville neighborhoods. You'll be close enough to pay a visit to the Sears (Willis, if you must) Tower, John Hancock Building and Millennium Park. A short walk will provide you endless shopping on the Magnificent Mile and allow a beautiful stroll along the lake. Multiple "el" stops in the area can connect you to other popular parts of town as well. No more than stumbling distance, all of your nightlife desires will be met along Hubbard Street or in the nearby "Viagra Triangle".
Don't rent a car
The city of Chicago thrives on punishing those with a car. Parking at a hotel will cost you an average of $50 per night. Parking meters will run you $6.75 per hour, the most expensive meters in North America, and keep you running back to your car every 2 hours to repay the meter. It's a commuter city. Most of the residents get around just fine every day without a car and you can too. The transportation system is superb, accessible from most neighborhoods, and easily navigated.
Don't feel like taking the train or bus to dinner? No problem! Taxis are also easy to flag or consider using Uber to schedule a pickup without any delays.
Don't pay for a visit to the John Hancock Observatory
Now the fourth tallest building in Chicago, with the Trump International Hotel's recent completion and claim at second, this frequently visited building provides some of the best views of the city. But you need not pay $17.50 to wait in line and admire the views from the 94th floor. Instead, plan to grab a drink at the Signature Room on the 95th and 96th floors. If you're patient enough or can plan to attend during an odd hour, you can secure a table right at the window and enjoy the undisturbed view for as long as you'd like with the comfort of your favorite beverage.
Don't bother stopping at Navy Pier
Unless you are towing children who live for ferris wheels and acrobat shows, don't devote time to Navy Pier. While it's free to visit, this over crowded piece of land right on the lake is the definition of a tourist trap. The same views can be found many places along the lake without the pressure to purchase churros, cotton candy and Chicago themed t-shirts.
The one exception to this rule, is if you plan to go on the Chicago Architecture Tour up the Chicago River. This is one of the most amazing ways to learn about Chicago and you generally board the boat from Navy Pier.
Don't eat at a chain restaurant
Chicago has an incredible food scene. Where small plates and social atmospheres are now the norm, we have access to esteemed chefs who cook with personality and set out to entertain. While your typical chain restaurants have strategically placed themselves on the busiest of corners throughout Chicago, a quick look down the block could land you in a better, true "Chicago" dining experience.