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A Vacation Guide to Chicago, Illinois

by Carianne Hixson
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The windy city could blow anyone away with its distinct blend of architectural beauty, history, and culture. Nestled along the southwest coast of Lake Michigan, Chicago, Illinois boasts a skyline that rivals New York City with water as clear as the Caribbean sea. The nation’s third largest city is home to the Chicago River, which glides through the heart of the city — giving it an uncommon European quality unlike any city in the nation. We’ve rounded up some history, facts, and things to do in this wonderful midwestern city. Read on for a guide of things to do in Chicago.

History + Facts

Incorporated as a city in 1833, Chicago was the nation’s opportunity to expand west. In less than a decade, it would become the nation’s railroad center as well as a hub for passenger and freight railway transportation. With its popularity growing, so did its population. The city worked diligently to make Chicago livable for its residents, installing a sewage system and constructing homes. Unfortunately, these homes would all be destroyed in The Great Fire of 1871. The entire city would burn to the ground from October 8th -10th, leaving more than 100,000 residents homeless.

The Great Fire of 1871 led to the Great Rebuilding of Chicago. A modern Chicago rose from the ashes, equipped with a grid system and innovative architecture better suited for the industrial world. This new Chicago would include places we know and love now such as Grant and Millennium Park. 

Read More: A Firsthand Experience of a Cross-Country Amtrak Trip

Getting There

Your best bet for transportation to Chicago would be by plane. It’s just a two-hour plane ride from EWR followed by a 30-40 minute Uber from O’Hare, which will get you right to the heart of downtown Chicago. 

If you’re feeling ambitious and want to try to drive it, it’s roughly a 13-hour drive. Cleveland is right on the way and breaks up the drive if you’re looking to make a stop along the way. 

Where to Stay

Downtown Chicago is the perfect place for first time visitors to stay. With an endless supply of top-quality hotels and Airbnbs, you’ll have no trouble finding a place to stay that is within walking distance to it all. We recommend being as close to the Chicago River as possible, as it’ll give you access to many of Chicago’s best districts — all by foot. 

What to Eat

Food is always a great place to start whenever traveling to a new place — and cities especially are packed full of so many dining options. Chicago in particular is known for having its own spin on certain dishes and, as they say, when in Rome. With staples like the Italian beef sandwich, deep dish pizza, and a Chicago hot dog, here are some noteworthy Chicago eats to try:

Al’s #1 Italian Beef | Multiple Locations

A staple of Chicago for over 80 years, the Chicago Italian beef sandwich was created by Italian immigrants who needed to stretch their supply of meat as far as it could go. This delicious sandwich is filled with thinly cut beef and strewn with giardiniera – a mixture of sweet and hot pickled peppers. It’s a simple recipe that packs a huge punch. Traditionally, this sandwich is dipped in an au juv and then served — but customers have the choice to have their sandwich fully dipped in sauce or served on the side. Al’s does it better than any other spot in the Chicago area. 

Fulton Market District

Unlike the typical tourist traps, Fulton Market District is a former warehouse district in Chicago that has transformed into a trendy place with tons of upscale eateries. Located in the North West Side of Chicago, Fulton Market District is now home to many corporate headquarters such as Mondelez, Motorola, and Vital Proteins, and it attracts many young workers to the area. Places to eat include the Time Out Market, Girl & The Goat (Top Chef winner Stephanie Izzard’s restaurant), and many more. We also enjoyed dinner at Lena Brava, an upscale restaurant celebrating classic Mexican flavors. 

Lou Malnati’s | Multiple Locations

Nothing is more controversial to a New Jersey native than Chicago’s deep dish style pizza. From its thick crust, to its layers of cheese and meat, Chicago deep dish pizza seems more like a pie than a pizza. Not meant to be eaten casually, deep dish pizza requires you to sit down with a fork and knife. As you cut through the layers of melted cheese and simmering red sauce, you understand why Chicagans are so proud. This pizza is a delicacy; the perfect antidote to cold winter days in the windy city. One slice should suffice, and leftovers are just as delicious. Of all the deep dish pizza locations in Chicago, Lou Malnati’s is truly a must-visit. 

Portillo’s Hot Dogs | Multiple Locations

Chicago-style hot dogs are a pride of the city’s people. Unlike the New York dog, these are served on a poppyseed bun, dressed in mustard, relish, diced onion, tomato, sport peppers, and a dill pickle. The cacophony of flavors seem nearly impossible to work together, yet it does. And the speed with which the team at Portillo’s works to serve these hot dogs makes it even more impressive. 

See More: A Weekend Getaway to Westerly, Rhode Island

Things to Do

The Bean | 201 E Randolph Street

Located in Millennium Park, Cloud Gate — better known to tourists as The Bean — is a public sculpture made of 168 pieces of stainless steel welded together. Built between 2004-2006 by Indian-born British artist Anish Kapoor, The Bean, inspired by liquid mercury, is a reflective piece in every sense of the word. Acting as an art piece as well as an optical illusion, this iconic sculpture excites the mind through its infinite reflections. When viewed at the right angle, The Bean reflects the skyline of the city of Chicago. 

Chicago Riverwalk

One of the most charming aspects of Chicago is its walkability. The Riverwalk is an open-air, pedestrian-friendly path that runs along the river. The Riverwalk offers visitors a cinematic view of the downtown area unlike any other city. Strewn with restaurants and cafes, visitors can dine along the waterfront or trek to the Riverbend where there is grass for laying and lawn chairs for relaxing for all to enjoy, free of charge. You will also see dozens of boats passing, as cruising the river is one of the most popular tourist attractions of the city. 

Navy Pier | 600 E Grand Avenue

Situated on Lake Michigan’s shoreline, Navy Pier is a 3,300-foot-long pier that extends into the lake. A top tourist attraction, Navy Pier offers restaurants, parks, amusement rides, museums, and so much more. Opening in 1916, the pier has gone through many iterations of itself but holds strong as a top destination for visitors and residents alike. Navy Pier is one of the more family-friendly destinations in Chicago.

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