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.

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.

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.

Posh/trendy:

  • 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

Cheap:

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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Do you have any tips on what to do in Chicago?

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63 thoughts on “What to Do in Chicago (A Locals Guide to Eat, Drink, Stay, Explore)”

  1. Jeremy Branham

    It’s been many, many years since I’ve been to Chicago. Great tips and glad she included the Cubs at least (White Sox fans won’t be happy). I had the chance to attend a game at Wrigley many years ago. However, there are still many thing I never did in Chicago. I need to make a return trip there as an adult and see how much the city has changed.

    Thanks for the tips Lisa. Great to see a fellow Gamecock grad so successful and proud of her city! 🙂

    1. G’day Jeremy,

      I’m a BIG Chicago Bulls fan. And love that they have all the major sports teams. And throw in the food, architecture, parks etc and I could live there (summer months) 🙂

  2. Great post! My brother lived in Chicago for a while and I always had a great time visiting him. Chicago is the largest city I’ve visited, so I don’t have anything to compare it to, but I agree that it is much greener and cleaner than I would expect a large city to be.

    This may be a bit touristy, but taking a river tour of Chicago’s architecture is another “to-do” I’d recommend. It’s incredibly interesting and loads you with fun facts to tell your friends 🙂

    1. Thx Lauren! Yep–totally agree on the Chicago Architecture Foundation’s River Tour (as mentioned above)…it’s a great way to see downtown and learn about all the amazing architecture!

  3. Definitely Hot Dougs and Big Star.
    For drinks, the Aviary, the Whistler, and Scofflaw
    For foood, Longman and Eagle,

    1. Hey Alex-
      Thanks for chiming in! Big Star has become a great place to take visitor’s since it’s slightly off the beaten (downtown) path and has that great, huge patio for eating and drinking! And Hot Dog’s (albeit so popular) also seems like a hidden find!! I have to try Longman and Eagle again…for some reason just wasn’t impressed the 1st time!

  4. Hands down best online guide to Chicago I’ve read yet – BOOM! 🙂 As a native of Chicago I can confirm that Lisa has absolutely NAILED it. What I think speaks for Chicago is truly the way that people who live in the city love it, talk it up, brag about it and want you to visit. I would say of all the things i agree with (and that’s the whole article) getting out into the neighborhoods is the best part of visiting Chicago. They are so fun and varied, and there are still so many local joints to hang out or shop in. Great post!

    1. Wow…thanks Jess!! So true – I’m always really trying to convey to people how it’s the one place that I’ve lived where it seems everyone loves it and makes it known.
      Can’t wait to meet you guys. When are you in town?

  5. Daniel McBane

    Very thorough post. I lived in Chicago for a year about 10 years ago and I can’t think of anything you missed. I’m glad you didn’t specifically mention the deep dish pizza, as I a always thought it was one of the worst things anyone has ever done to what started out as a great food. I did however love Chicago Style hotdogs and still get the occasional cravings for one even to this day.

    1. Hi Daniel! Thanks for your comments! Yeah, I’m a Jersey girl at heart (grew up there) so I am not shy about saying that Chicago Pizza is the ONE thing I do NOT like there!!! It’s just too much of everything – like a loaf of bread with sauce on top! I still stay true to my NY pizza roots!
      But after living in Chicago now 13+ years, it is my home and I love everything else about it and can admit that I think it’s better (and easier to live in) than NYC!

  6. Very thorough, user-friendly post on Chicago, one of our favorite cities in the US. The Institute of Art, the opera and the Field Museum are three of the places we always make sure to visit while in town. Also check out Boystown, which is considered the first officially recognized gay neighborhood in the entire country. The Chicago deep dish style pizza is not to be missed. 🙂

  7. Really enjoyed the blog. I’ve visited three times and enjoyed it more each time. I stayed at the HI Hostel which is one of the best I’ve ever been to. And the Billy Goat Tavern near the Tribune Towers was fabulous, as was the aquarium.

  8. I came across your blog while searching for filter for my Canon 650D camera. Amazing blog, makes me want to visit Australia. You guys rock, nice family too :)!

  9. Came across your site while researching our upcoming trip to Chicago! Fabulous site! Question though…. what is the link to your place on airbnb? I’d love to check it out. Thanks!!

  10. I visited chicago many times some years ago. Love the city and it’s momentum. The only thing I didn’t like was that a lot of people there drive like maniacs.

  11. Thank you very much for publishing such resourceful blogs about tourism. What a nice opportunity to know about the beautiful tourist spots and lodging options. It is opportunity to aware our visitors who used our services of luxurious Limousine during their vacations. http://www.aboutchicagolimo.com

  12. Craig,

    You gotta check out this new iPhone app named 312Go.

    The app tracks your location through the city and triggers fun audio bytes about the sites you’re passing, as you pass them.

    I love using it while running.

    Thought I knew the ins and outs of the city, and it turns out their are still countless stories I’ve never heard.

    Strongly suggest it to anyone… really hoping it catches on.

  13. Thanks for your blog really great and useful as I m going to chicago next saturday….would y know by any chance a good bar with live music ? Jazz…?
    Thanks

  14. Thanks so much for this wonderful article. I am thinking of relocating to Chicago and this guide will be a great way to kick off my exploratory trip this summer. Lincoln Square is exactly the neighborhood I’m considering for apartment hunting!

  15. I love Chicago. I go there at least once a year for a convention and it is a great city with plenty to do. I would move there, but it gets so cold in the winter. But it is a wonderful city.

  16. Great guide – Chicago is one of the greatest places to live and to raise a family. If you plan on coming and doing any touristy things, the best time is during the week. Certain spots can be very crowded during holidays and weekends.

  17. Love these tips. I’ll be going to Chicago in a couple of weeks. Only for two days though. I’ve been there once before but loved it! Trying to plan things to see and do in a short period. Thanks for the info!

  18. 2012 in Chicago. So now that it is 2014, I am guessing I won’t be able to find you on Airbnb? I am looking on the site and if you still own an apartment there, shoot me an email please! I am taking my husband on his 30th birthday trip to Chicago. This post was extremely helpful by the way.

  19. Noreen Greenacre

    Really enjoyed your blog! I am visiting Chicago next month – a party of six adults. Can you recommend a tour company for a comprehensive good value tour of the city for around four hours as we are fairly time limited?

    Cheers!

  20. I love to travel and although I have visited MANY large cities across the U.S., Europe, and the Middle East, I still rank Chicago as the #1 city that has it all! One tip I did not see here is the Chicago festifal calendar. The City of Chicago website publishes its calendar year festival list reflecting the date, location, and themes. This can help plan an excellent trip – most events are free or have a very minimum entry fee that covers the cost of the residential fest permit. For those on a budget, be sure to check out a Chicago Public Library – you can “borrow” a free museum pass!! Finally, Chicagoans love trendy food and there is no one place for any one trend, but MANY new places to check out. Start with the Chicago Newspaper, the Chicago Reader (free in Chicago and they have an excellent website), to help navigate all of the trends. Have fun!

  21. Lovely Information, thank you. If we did bot plan a Trip already i would like to very much now. ;o)
    Do you have a Suggestion on how to get Tickets for a Basketball or Baseball Match? My Kids arme Great sportfans and would Love to See one .

  22. Awesome guide – tip of the cap! For everyone out there that wants to save a little cash in the Chicago (and who doesn’t?) make sure to check out Free Chicago Walking Tours – 2hr walking tours of Chicago’s most iconic neighborhoods and sites including the Loop, Chicago River, Mag Mile, Lincoln Park & Millennium Park.

  23. Amazing post, Thanks so much I just moved to Chicago and am still getting the lay of the land and your post has given me so much to consider! I am really looking forward to my family coming into town so we can explore this beautiful city! Thanks again.

  24. its really nice article with beautiful pictures. I went to Chicago last year on a weekend trip so I traveled 6 places in 3 days there which was really an awesome experience. I got really delighted reading this one.

  25. Seriously what a great rundown! I printed it out. 🙂 I just found out my husband is being relocated for his job to Chicago and its a big move for us! I am trying to be positive, but leaving friends, family and my own job is hard. I appreciate all the information and am optimistic that it will be a good thing! Thanks

  26. Born and raised in chicago,Lincoln, Belmont. Moved to tampa fl. 48years ago, but it’s always nice to go back to visit. Go visit Dinkels on Lincoln ave. One of the best bakeries in town
    Plus they have the best hots dogs in the country.

  27. Excellent! I am so glad that I stumbled upon your site! You have given so much wonderful information, I know I will be back again and again!

  28. YES! I have lived in Chicago for over 13 years and still love everything about it. So much so that I am the owner of a Chicago vacation photography business, Wallflower Studios. Our photo shoot walking tours are at popular spots like Millennium Park, The Magnificent Mile, Navy Pier, and more. However, I am always looking for more and more ideas to share with visitors of Chicago to ensure they experience everything our great city has to offer.

    Thank you for this list! This will also help people become a tourist in their own city when things open back up after Covid-19.

    Andrea
    http://www.wallflower-studios.com

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