How to Spend 48 Hours In Chicago

Harry Jackson
How to Spend 48 Hours In Chicago
Author: Harry Jackson
17.04.2019 18:19PM

Have you ever met someone that has not utterly loved Chicago? Come on, Frank Sinatra even wrote a song about it!

You're almost guaranteed to fall in love with Chicago when you're there too, and it’s easy to see why. Chicago is full of history, culture, blues music and arguably the best food in the United States!

But how do you make the most of Chicago in a short visit? Here at Smaller Earth we've come up with an amazing itinerary for how you should spend 48 hours in this amazing city.

Day 1, 9am - Lake Shore Drive

Grab a coffee and take an early morning stroll along Lake Shore Drive as a trip to the windy city isn't complete without this iconic walk. With the homes of Chicago’s elite on one side and the impressively vast and blue Lake Michigan on the other, you'll soon discover why this is a must-see when travelling in Chicago. It is also a great spot to do some people watching (and you'll get some serious house/apartment envy too). Many celebrities live on Lake Shore so you may even get lucky and see a star! On your walk, you’ll also find stunning parks, public exercise gyms and plenty of quiet spots just to hang out and take it all in.

Day 1, 12pm - Willis Tower Skydeck

The Chicago skyline is dominated by the Willis Tower. Wait the Sears Tower? Yes, but no. The Willis Tower was known as the Sears Tower until 2009 when the name changed to the Willis Tower. The Willis tower was once the tallest building in the world, until the World Trade Centre was completed in New York City in 1970. Take the short elevator ride to the observation deck to see some of the best views of Chicago. With unbelievable views of Lake Shore Drive, landmarks including the Navy Pier and Soldier Field, it'll easily become one of your favourite spots in Chicago. If you're brave enough, you can take a walk out onto the Skydeck (an enclosed, glass balcony that hangs over the edge of the tower). Seeing Chicago from 103 floors up is well worth doing if you fancy an adrenaline rush!

Day 1, 2pm - Check out a game

From Baseball, to Ice Hockey, to American Football, Chicago has a huge sporting culture. No matter what time of year you visit Chicago, you have to go see some sport! Whether it be the Chicago Cubs or White Sox for baseball, the Chicago Bears for football or the Chicago Black Hawks for Ice Hockey, you are guaranteed a fun evening at whatever game you go to.

Smaller Earth recommendation: Keep in mind that tickets for Football games can get pretty pricey, so definitely look into in advance if this is your sport of choice. However, if you're looking for cheaper options, baseball may be the game for you! Check out StubHub and SeatGeek and you will find plenty of great seats at reasonable prices.

Day 1, 8pm - Kingston Mines

Chicago is the home of, and therefore has the best, best blues music in the world (an undisputed fact). You should definitely spend one evening at a blues club, and why go anywhere else other than the Kingston Mines? Kingston Mines is the oldest continually running blues club in Chicago. The club has two stages, allowing the music to go on non-stop all night, every night! Entry to the club costs $12 on Sundays and $15 on any other day so it won't break the bank balance either. Think about it, for two bands and non-stop music until 3:30am, that’s amazing value! Get down to the Mines during your Chicago trip, for one of the best music experiences of your life, guaranteed.

Day 2, 9am - Route 66

Morning! fact- Route 66 actually starts in Chicago! The iconic road starts on Adams Street and goes all the way to the Santa Monica Pier in Los Angeles, California. This is one of those ‘touristy’ things you have just got to do whilst you are in Chicago! Not only can you head to Adams Street at Michigan Avenue to see the start, but also if you go just one block over, you can see the end point on Jackson Street at Lake Shore Drive.

Day 2, 10am - The Bean

Just a 7 minute walk from Route 66 and you'll reach another iconic Chicago landmark; the bean. This huge, reflective sculpture is impressive so be sure to walk underneath it to see the crazy reflections on the inside of the curve. The bean is located in Millennium Park which is an absolute must-do when you travel to Chicago. From it's lush open parks, to it's huge open air concert hall, you may even catch a show if you're lucky! Next to Millennium Park is Grant Park, where you’ll find more open space, the Buckingham Fountain and the art institute of Chicago. Explore the parks on a Chicago city bike, or walk at your own pace listening to Frank Sinatra sing about how great this city is.

Day 2, 11am - Magnificent Mile

Whats a big city without it's shopping, right?! In Chicago, you’ll find all the major stores along the Magnificent Mile on Michigan Avenue. Grab some lunch and window shop your way down the Magnificent Mile. You’ll find everything from clothing, to computers, to candy and see some of Chicago's best architecture in between. Start next to the John Hancock Centre and head down towards the river, seeing the Wrigley building and Trump Tower. Don’t fancy walking? Take the bus! There are plenty of open bus tour operators to choose from, that will take you up and down the mile at a leisurely pace.

Day 2, 3pm - Lincoln Park Zoo

Everyone loves a zoo. A free zoo? Even better! Catch the “L” (elevated train line) to Armitage Station (brown and purple line) and take the short walk west to the zoo. In the zoo (did I mention is was free?!) they have some incredible enclosures. From polar bears to gorillas, crocodiles to chameleons, the Lincoln Park Zoo has it all! Not only does it have impressive enclosures, but you get an incredible view of the city from there too- so make sure to bring your camera!

Day 2, 7pm - Navy Pier

Nothing screams Chicago more than Navy Pier! Navy Pier is over 100 years old and is still a hit with the locals and visitors alike. Along Navy Pier you’ll find restaurants, shopping malls, theatres, amusement parks, arcades, it’s like it’s own little town! If you ever get down to Navy Pier, there is an amazing hotdog joint selling different styled hotdogs from all over the USA. But there's one rule... no ketchup! This is a Chicago tradition, absolutely no ketchup on hotdogs. You won’t even find any ketchup in the condiment section to prevent any pesky customers trying to get some ketchup on their dog.

Want new travel guides sent directly to your inbox?

Subscribe to the Smaller Earth Newsletter.

Get in Touch