What to Do in Chicago

22 May

Looking for travel tips on what to do in Chicago?

As part of our city guides series we interviewed Lisa Lubin who moved to Chicago in 1998 because she accepted a job as a producer with ABC-TV in Chicago.

As a TV producer, it was her job to cover all the fun stories of the city – the restaurants, bars, travel, fitness, attractions, and she got to know the city better than most natives.

Lisa share’s with us her insider tips on what to do in Chicago for those looking for the best things to see and do, where to eat, stay, drink, and play.

Take it away Lisa…

Why Visit Chicago?


what to do in chicago

Chicago at dusk

I truly believe (and it has been confirmed by others) that Chicago is the best city in the United States to visit or live in. Boom. Hands down victory.

Seriously, New York is great and I’m from that area, so it did take me awhile to admit it out loud, but Chicago has everything NYC has, except it’s cleaner, greener, and more friendly. Plus it’s just easier to live in.

And for a traveler, it’s a wonderful place to visit to see world renowned architecture (with one of the best skylines in the world), world-class museums, parks, food from around the world, and the amazing and huge lakefront (Lake Michigan is so big that we can’t see the other side, so it appears we are on an ocean).

What to Do in Chicago?

Millennium Park Chicago by LL

Frank Gehry Bandshell at Millennium Park


Millennium Park

This is an amazing art-filled park right downtown. See a free concert, snap photos of the “Bean”, check out the video fountains, just enjoy the gardens, or grab a beer at vast outdoor beer garden at the Park Grill.

The Loop

This is 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 (Sears) Tower, the Jeweler’s Building, the Cultural Center, the Thompson Center, The Board of Trade and more. For a different view, take the Chicago Architecture Foundation’s boat tour on the Chicago River.

Michigan Avenue

This is Chicago’s most popular shopping street. Michigan Avenue’s 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 (a building I had the pleasure of working in a couple years ago).

Tribune Tower Chicago

The Tribune Tower


Chicago Lakefront

One of my favorite parts of the city is our huge, ocean-like lakefront. 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.

Lakefront Path


Museum Campus

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

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.

Wrigley Field

The Home of the Chicago Cubs


Where to Eat in Chicago?

My favorite thing to do in Chicago? Eat.

Chicago has hundreds of restaurants and bars of all varieties and ethnicities. From Ethiopian to Thai to sushi to Peruvian, you can just about find anything. I could make list upon list of where to eat, so here are just a few ideas.


Sushi at Macku


Some affordable, yet tasty spots:

  • Hot Doug’s
  • Kuma’s
  • Xoco
  • Cozy Noodles
  • Ba Le
  • Big Star
  • Belly Shack

For a splurge try:

  • The Girl and the Goat
  • Sunda
  • Japonais
  • Frontera Grill
  • Purple Pig

Great areas for Ethnic, local joints:

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

Where to Drink 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.


  • Signature Room
  • The Wit
  • Many bars along Hubbard Street

Sports Bars:

  • The Globe Pub for soccer/football
  • Wrigleyville Bars

Great outdoor space/rooftops:

  • The Wit Hotel Roof
  • The Terrace at Trump Tower
  • Studio Paris
  • Vertigo Sky Lounge
  • Park Grill
  • Gene’s Sausage Shop
  • Pegasus Rooftop
  • Sheffield’s Beer Garden
  • Moody’s Pub

Best Place in Chicago for a Night on the Town?

Chicago’s live theatre scene rivals New York’s. For a great 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.

Where to Stay in Chicago?


  • Hostelling International Chicago
  • Arlington Road Hostel
  • Airbnb at my place!

The Opposite of Cheap:

  • Four Seasons
  • The Peninsula
  • The Wit
  • The James
  • Park Hyatt
  • The Ritz-Carton

Chicago Markets and Shopping Districts?

Michigan Avenue is our 5th Avenue, but prettier. Gorgeous Christmas decorations in winter and flower-filled parkways in spring and summer.

Oak Street is 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.

How to Get Around Chicago?

Public transport is great in Chicago – so much so that I do not own a car. To get around, I simply either walk, ride my 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 $2.00 and $2.25 respectively. Keep in mind this money saving tip: For one fare, you can transfer two times in a two hour period.

Is Chicago WiFi friendly?

Free Wifi is becoming more and more prevalent. Many cafes offer free wifi, look for signs in their window – the easiest to find would be of course, Starbucks which all have free wifi and are just about on every corner.

All Chicago libraries have free wi-fi and there’s always the Apple Store on Michigan or North Avenues.

Best Time of Year to Visit Chicago?

Personally, I like all seasons, but yes, we can have a very cold winter which is often below freezing. 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 – between May and September or October.

Getting There and Away?

Chicago has two airports – O’Hare International and Midway – and both are connected easily to the city by the CTA train for just $2.25. It’s super easy and cheap.

Chicago is 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 – for example a one-way to New York City recently cost me just about $90.

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.

Best “insiders” tip for travellers?

For a great view of the city for the price of a drink, skip the observation tower fee and go to the Signature Room Lounge on the 96th floor of the John Hancock tower.

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)

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:

Armitage Avenue – boutique shops

Belmont – want a piercing or tattoo to remember your visit to Chicago? This is the place for that…and other fun fringe stuff – sex shops, boystown, and as always, great food.

Southport – get off and walk north for lots of bars and restaurants in this cute Lakeview ‘hood (where I happen to live)! Come say hello!

Western – take a wander into one of my favorite ‘hoods, 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.

I love Chicago because _________?

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 it 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.

What to Do in Chicago


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