13 Unmissable Things To Do In Chicago For First Timers

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Chicago is a wonderful place to visit to see world renowned architecture (with one of the best skylines in the world), world-class museums and public art, beautiful parks, taste amazing food from around the world, and experience the vastness of Lake Michigan.

When it comes to finding things to do in Chicago, you’ll never run out of options. That’s the beauty of this city. It’s so dynamic and diverse, that each time you visit, there’s always something new and exciting to explore.

If it’s your first time in Chicago and you’re not sure what to do, then in this guide I present to you the most unmissable attractions for any first time visitor, which will help you get a sense of the city and see it’s most iconic landmarks.

Unmissable Things To Do in Chicago

1. See the art in Millennium Park

This is an amazing art-filled park is right in the heart of downtown Chicago.

See a free concert, snap photos of Cloud Gate, also more widely known as The Bean, just enjoy the gardens, or grab a beer at vast outdoor beer garden at the Park Grill.

There are also some iconic fountains in Millennium Park to check out. Crown Fountain is part fountain, part interactive artwork, and features a video sculpture behind a waterfall.

There is also Grant Park and Wicker Park, which are two much loved urban parks in the city.

2. Check out the architecture in The Loop

The Loop is what’s known as the heart of the business district. During the week it’s full of workers scurrying about.

The area is full of some great architecture like the Willis Tower (Sears Tower), the Jeweler’s Building, the Cultural Center, the Thompson Center, The Board of Trade and more along the Chicago Riverwalk trail.

For a different view, take the Chicago Architecture Foundation’s boat cruise on the Chicago River.

For amazing architecture, duck inside these buildings in The Loop for neat interiors (don’t forget to look up):

• The Rookery
• The Thompson Center
• The Cultural Center
• Macy’s (has a Tiffany Ceiling)
• Inside the Starbucks on Michigan Avenue

3. Walk down Michigan Avenue

Michigan Avenue is Chicago’s most popular shopping street. The most popular stretch is just about a mile long (hence it being called the Magnificent Mile) and full of all the favorite shops like Macy’s, Nike, the Disney Store and the Apple Store.

Plus don’t miss two of my favorite buildings – the beautiful Wrigley Building and it’s neighbor just across the street, The Tribune Tower.

4. Visit Chicago Lakefront

One of my favorite things to do in Chicago is visit the huge, ocean-like lakefront. Walk along the lakefront trail or charter a boat out on Lake Michigan – there are many ways to enjoy the lake.

On warm, sunny days folks of all kinds will be out enjoying the lake by running, cycling, roller blading, boating, walking or just sunning themselves.

Rent a bike and ride for miles north from Navy Pier, through Oak Street Beach, to North Avenue Beach (stop for a beer and a burger at Castaways at the Boat House), watch some volleyball and enjoy the view of the city.

5. Stroll around Museum Campus

A place for a beautiful stroll (and one of the best skyline views in the city), is the museum campus.

It has some of our great museums from the Adler Planetarium to the Shedd Aquarium to the Field Museum of History.

And right nearby, you can’t miss the Art Institute of Chicago.

6. Explore the Chicago Neighborhoods

Chicago is a city of neighborhoods. Nothing will give you a better feel for the real city than getting out of downtown by just a couple of miles and venturing into the ‘hoods where real Chicagoans live, work, and play.

My favorites are the village-like areas of Lincoln Square and Andersonville.

A stop in Wrigleyville is a must to see Wrigley Field (the second oldest baseball field in the U.S.) plus the neighborhood is full of fun bars and restaurants.

Get on the Brown Line and ride north until the end. You will pass through lots of Chicago’s young and trendy neighborhoods where many folks actually live.

Good stops to get off at for a stroll are Armitage Avenue for boutique shops, Belmont for an alternative scene. Want a piercing or tattoo to remember your visit to Chicago? This is the place for that…and other fun fringe stuff.

Southport has lots of bars and restaurants and has a cute Lakeview vibe.

Western is one of my favorite ‘hoods, and home to the charming Lincoln Square. The former German neighborhood is now an eclectic area that still retains a bit of European flavor in its main square and outdoor cafes.

Grab an amazing pastry at the Austrian Cafe Selmarie, sit in the sun with a beer on the rooftop of Gene’s Sausage Shop, or settle into a good book and glass of wine (and free wifi) at the locally-owned Book Cellar. Pure Chicago in one ‘hood.

7. Check out views from a skyscraper

My best insider tips on what to do in Chicago would be for a great view of the city for the price of a drink.

I recommend you skip the Chicago Observation Deck fee and go to the Signature Room Lounge on the 96th floor of the John Hancock Center. You get amazing views, but at a fraction of the price.

Another popular place for views is Willis Tower Skydeck, also known as Skydeck Chicago, which is a place to go for the adventurous people. On the 103rd floor, you can walk out onto a glass box deck, located 1,353 feet above the floor and extending by 4.3 feet.

The Ledge, as it’s called, is the place to go for an aerial view of Chicago, if you have the legs for it!

8. Hit the bars in Chicago

Like restaurants, there is no shortage of bars in Chicago. If the weather is nice be sure to go al fresco and try one of the great rooftop bars, beer gardens, or sidewalk cafes.

For posh and trendy places with excellent cocktails and a sophisticated vibe, check out the Signature Room and The Wit at Hilton Hotel, plus there are many bars along Hubbard Street. If you prefer sports bars, check out The Globe Pub for soccer/football.

Some great bars with an outdoor space/rooftops are Terrace 16 at Trump Tower, Studio Paris and Pegasus Rooftop.

Some other great full service restaurants with a great garden are Park Grill, Sheffield’s Beer Garden, and Moody’s Pub.

9. Explore the theatre scene

Chicago’s live theater scene rivals New York’s. For a great broadway show, check out the many theatres in the Loop that are part of “Broadway in Chicago.”

For discount tickets, go to Hot Tix.

Dozens of famous comedians such as John Belushi, Gilda Radner, Bill Murray, Dan Aykroyd, Mike Myers, Chris Farley, Stephen Colbert, and Tina Fey came out of Chicago’s Second City. Go for a great comedy show.

10. Go shopping in Chicago

For shopping, head to Oak Street, just at the north end of Michigan Avenue. This is where you go to window shop, as you’d need a lot of cash to drop here on name brands like Gucci, Prada, and Barney’s New York.

State Street has been revived as that “great street.” Starting south of the river, you can find tons of affordable shopping here at popular shops like Old Navy, Forever 21, and the grand Marshall Field’s Department store (now Macy’s).

If you are here in summer, don’t miss the Green City Market up in Lincoln Park every Saturday.

11. Tour a Frank Lloyd Wright home

If you’re a fan of architecture, then you’ve come to the right city. Chicago is well known for having some of the best examples of modern architecture in the United States, and a pioneering architect that’s world famous, is Frank Lloyd Wright.

Oak Park is where the majority of Frank Lloyd Wright homes can be found, but you will also find some excellent examples in Hyde Park and Downtown.

The best way to learn about his life and legacy, as well as see his architectural wonders, is on an architectural tour. You can tour his home and studio, the Rookery, Unity Temple or Frederick. C Robbie House. Check out tours here!

12. Watch a band at Green Mill Jazz Club

One of the most iconic clubs in the city is Green Mill Jazz Club, which is open to guests every night of the week and have live music every night.

They are open later on Fridays and Saturdays, and also have a restaurant.

On the third Sunday of every month, they have an Uptown Poetry Slam Sundays event.

This is a cash only bar. Check out the what’s on calendar to see who’s playing when you visit.

13. Check out the National Museum of Mexican Art

Opening its doors in 1982, the National Museum of Mexican Art in Pilsen is the only museum dedicated to the Mexican community of the USA.

The 48,000 square-foot facility is home to 3,600 years worth of artwork from both sides of the border.

Visitors can admire Mexican art in all forms, from photography to textiles to theater and film.

Each year in September, the Pilsen neighborhood hosts one of the country’s largest Mexican Independence Day celebrations.

Where to Eat in Chicago

One of the best activities you can do in Chicago is eat. Chicago has hundreds of restaurants and bars of all varieties and ethnicities. Of course it’s famous for its deep-dish pizza, but there is much more than that.

From Ethiopian to Thai to sushi to Peruvian, you can just about find anything from all corners of the world.

Here are just a few ideas of some places to eat. For some affordable, yet tasty spots, check out:

For a splurge try:

Great areas for Ethnic, local joints:

• Devon Avenue for Indian
• North Broadway for Ethiopian
• Argyle Street for Vietnamese
• Milwaukee Avenue for Polish

How to Get To and Around Chicago

Chicago has two airports, O’Hare International and Midway, and both are connected easily to the city by the CTA train. It’s super easy and cheap to get to the city via the train.

Chicago is also the home of United Airlines, so there are tons of their flights here.

Southwest is one of my favorite options for cheaper flights between Chicago and many other U.S. cities. Their online fares can be very cheap. You can also take the Amtrak train to and from Chicago to other cities in the USA including all the way to California.

There are long distance buses as well, including the cheap ride, Mega Bus (with hit or miss reviews) to many other mid-western cities.

When it comes to getting around, public transport is great in Chicago – so much so that you don’t need a car.

To get around, simply either walk, ride a bike, or use the trains or buses. You can take the “L” also known as the CTA (Chicago Transit Authority), most places you will want to go.

Buses and trains use the same “CTA card” (that you can get out of a machine at the airport when you arrive) and fares are respectively low-cost.

Keep in mind this money saving tip: For one fare, you can transfer two times in a two hour period.

Best Time of Year to Visit Chicago

Personally, I like all seasons, but Chicago can have a very cold winter which is often below freezing. Especially as Chicago is famous for its wind, which gets bitterly cold in the winter – it’s not called The Windy City for no reason.

The snow is pretty at Christmas time and there’s ice skating and the amazing German Market in Daley Plaza.

But for the most comfortable times of year, I would say Spring, Summer, and Fall are great times to visit Chicago – between May and September or October.

Final Thoughts

I’ve never lived anywhere else where so many residents love their city. And I’ve never met a traveler that didn’t fall in love with Chicago as well.

It’s very likeable – clean, friendly, fun, youthful – there is a great energy here and yet so many are down-to-earth in their Midwest mentality.

There is a great pride here – everyone knows we live in a great place and it’s an infectious attitude. When it starts to get warmer, everyone comes out to enjoy this wonderful, gleaming city by the lake.

Even after traveling the world, I still can’t get enough of it.

Tours in Chicago

Where to Stay in Chicago

Kalyra and I stayed at the Cambria Hotel and Suites (the Magnificent Mile location), and the location was excellent.

We were a couple of blocks south of the river and only a five-minute walk to Millennium Park. It’s also right near public transportation, such as the “L” train line.

The rooms were comfortable and quiet and the bathroom large and the shower good – priorities. Kalyra commented several times how much she liked the hotel.

We were so busy we didn’t use any of the facilities but they also have fitness center, a bar and a restaurant.

See prices and availability for Cambria Hotel and Suites here!

You can also use the map below to find your ideal vacation rental or hotel in Chicago.

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