MidwestTop City Vacations

The Locally-Approved Beginner's Guide To Chicago

By , August 20th, 2014

Chicago…it’s my kinda town and it will be yours too in no time. This world-class city sits on the shores of tremendous Lake Michigan (so big, it looks like an ocean) where visitors are delighted by its lakefront beaches and parks, incredible restaurant scene, and world class museums.


What to Do

Cloud Gate Chicago, IL.

Chicago’s giant Bean sculpture . Photo by Vincentdesjardins CC BY

A first time visitor must head to Chicago’s newest outdoor space, Millennium Park, right downtown where you can see free concerts at the Frank Gehry-designed band shell, dine al fresco in the lovely beer garden (or ice skate right here in winter time!), and of course check out the wondrous and selfie-worthy reflective sculpture known as the “Bean”.

Lake Michigan Chicago bike ride

Bike along Lake Michigan. Photo by Ashley Williams

Rent a bike at one of the hundreds of stations all over the city and head to the lakefront path for a ride past volleyball courts, harbors, a golf course, and even a wildlife sanctuary. Hit the water by taking a boat tour on either the lake or the Chicago River where you will marvel at Chicago’s incredible architecture and massive skyline.

Hair-raising views

Willis Tower Chicago, IL.

Terrifying view down the Skydeck Chicago. Photo by Charlotte.Morall CC BY

For a bird’s eye view of the city, head up inside one of North America’s tallest buildings, the Willis Tower (formerly Sears Tower) to the new Skydeck Chicago for some hair-raising views.

Local’s Neighborhoods

Where to shop in Chicago, Il.

Tulips lining the Magnificent Mile. Photo by Multisanti

A stroll on beautiful Michigan Avenue is a must-do for shopaholics.

Wicker Park Chicago

Take a coffee break and chill with the locals. Photo by ercwttmn 

Every neighborhood has its own local and unique flavor–If you have time, check out some of my favorites like hipster hangout Wicker Park, baseball-themed Wrigleyville, Swedish-centric Andersonville, and heavily German influenced Lincoln Square.

Where to Eat

Cheap Eats in Chicago, IL.

The flavors of Chicago are alive, even in the hotdogs. Photo by Dishingupdelights CC BY

Over the last decade Chicago has grown into one of the world’s best cities for dining. This city literally has it all – from Thai and Greek to Ethiopian and Vietnamese, nearly every ethnicity is represented here. Plus there’s something for every budget from the famous Chicago Deep Dish pizza, hot dog stands, and corner noodle shops to Michelin Star and James Beard Award winning chefs and bistros.

Something for every budget

Affordable gourmet Mexican food Chicago, IL.

Sample a bit of Mexican heaven at XOCO. Photo by Suzieedwards CC BY

If you’re staying downtown, a stop in at Rick Bayless’ XOCO is a must for some affordable gourmet Mexican cuisine. There will likely be a line at this popular, counter-service spot, but it’s well worth it when you sink your teeth into the guacamole, amazing tortas, and decadent Mexican hot chocolate.
For that once in a lifetime’ treat, make reservations at Girl and the Goat, overseen by Top Chef winner, Stephanie Izard. The vibe is warm yet industrial and the food is some of the best around, really showcasing what the Chicago food scene has to offer.

Where to Sleep

Chicago has tons of hotels to choose from and more and more go up each season. Whether you’re looking for a simple budget option, a business hotel with all the amenities, or more of a cool, destination hotel with great bars and restaurants, Chicago has something for everyone.

Looking for the best places to find shelter from the wind of Chicago? Check out our trivago picks for best Chicago hotels

Chicago, IL. Skyline

Photo by Trump International Hotel and Tower with permission 

Some of the newer, luxury hotels include the brand new Langham, built into the landmark IBM building with a mid-century vibe right on the river or the Trump International Hotel and Tower. Find out more about staying at the Trump here!

Hotels in Chicago, Il.

Photo by Trump International Hotel and Tower with permission

There’s been a wave of new, boutique hotels as well. The James and theWit are a bit more trendy, but even if your budget doesn’t allow a stay there, head up to the rooftop bar at theWit for a crafted cocktail and some amazing views right in the heart of the Loop. If you’ve got your heart set on staying at theWit, see more info here.

Chicago hotels

Hang-out at the uber-cool theWit hotel. Photo by TheWittyOne

Local Tips

Rent a bike in Chicago
Photo by Tony Webster
  • Rent a Divvy bike. There are now thousands of bikes for rent located all over the city. Chicago has an extensive network of bike lanes on most streets and the fact that the city is completely flat makes it even easier to get around.
  • Take the CTA trains and buses everywhere. No need to spend money on taxis with a good network of trains.
  • If you need a taxi, try UberX. Just download the app to your phone.
  • Get out of the city center. Chicago is a city of neighborhoods, each one with its own unique vibe and charm. Take some time to head out and see where locals like to live and play.