What to Do in Chicago (A Locals Guide to Eat, Drink, Stay, Explore)

Looking for travel tips on what to do in Chicago?

As part of our city guides series, we interviewed local girl Lisa Lubin who moved to Chicago in 1998 because she accepted a job as a producer with ABC-TV in Chicago, and it was her job to cover all the fun things to do in Chicago – the best restaurants, bars, attractions and hotels.

What to do in Chicago - city guide
Need tips on what to do in Chicago? Image by Dreamstime.com

In this post Lisa share’s with us her insider tips on the best things to do in Chicago for those looking for the best places to eat, stay, drink, and explore.

Why Visit Chicago?

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 and public art, parks, food from around the world, and the amazing and huge lakefront with the lakefront trail (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

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.

There is also Grant Park and

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 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 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).

Chicago Lakefront

One of my favorite things to do in Chicago is visit 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.

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.

A Go City Chicago Pass will save you money on 30+ Top Chicago attractions. Pick the ones you want. 3 pass types to suit all travelers. Click here for more information

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.

a sign on a building
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.

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 for a Night on the Town

Chicago’s live theater 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.

Tours of Chicago (Sightseeing & Passes)

Get Your Guide

Is our preferred tour booking company for their great deals and service. They offer up to 24 hour cancellation, skip the line benefits and more. Check each tour for specific details.

See what tours and attractions are available for Chicago.

Viator tours

Viator is one of the industry leader when it comes to tours, activities, tickets and passes with a list of hand-picked tours and things to do in Chicago from local insiders.

Check out the Chicago City Pass which gives you discounted admission to five of the city’s premier attractions.

Chicago city pass

Be sure to compare with the Go City Chicago Pass, which may be the better value as it offers 30+ Top Chicago attractions and 3 different pass types. It depends on what you want to do and see. Click here for more information

Where to Stay in Chicago


The Opposite of Cheap:

Markets & Shopping in Chicago

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.

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 Travel to Chicago

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, 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.

Planning A Trip to Chicago

Accommodation in Chicago

  • Booking.com has over 200 properties in Chicago including hotels, apartments and hostels. You get free cancelation on most rooms and a best price guarantee.

Flights to Chicago

  • Skyscanner is a comparison website that searches millions of flights. Once you find your best deal, book directly through the airline (no extra fees).
  • Scott’s Cheap Flights have insane deals on flight prices.

Car Rental in Chicago

  • RentalCars.com is the world’s biggest car rental booking service that compares all the major brands like Hertz, Avis, Alamo, and Europcar. You probably won’t need a car for Chicago, but if you plan on any day trips.

Author Bio: Lisa Lubin is a three-time Emmy® Award winning television writer, producer/director, photographer, and video consultant.

She documents her (mis)adventures on her blog, LLworldtour.com, with photographs and articles from the road/train/rickshaw/camel. Her writing and photography has been published by the Wall Street Journal, the Chicago Tribune, Smithsonian and American Way Magazine. She recently launched LLmedia, a video consulting business.

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