The Ultimate Guide to Chicago: A Local’s Comprehensive List

If you’re looking for a guide to Chicago for an upcoming trip that is up-to-date and full of recommendations for bars, foods, landmarks, neighborhoods, and more – look no further. For the past 6 years we have lived in Chicago. And, though we travel around the world and country quite a lot, pre-covid, we spent a lot of weekends doing self-guided tours and bar crawls of our hometown. As local’s, we’ve got the inside scoop on what places are over-rated, what tours are worth it, and tricks to avoid crowds and lines.

Google Map

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Planning Your Trip to Chicago

Where to Stay in Chicago

If you’re a friend or family, well, the obvious answer is to come stay with us in Wicker Park! If not, well, then here are some cool neighborhoods to stay in:

• Chicago Loop: for first-timers who want the full city feel, skyscraper views outside their window, and walking distance to the bean
• River North: if you want the above but with more nightlife and dining options, and don’t mind walking south a bit to get to the bean
• South Loop: also very “downtown”, but closer to all the museums if that’s your thing
• Wrigleyville: if sports and drinking (great for bar crawls) are you two top priorities
• Lincoln Park: if you want to be a bit distanced from the skyscrapers and have access to the lake and parks
• Wicker Park: if you need a cheaper place to stay and/or have already done downtown and want to explore the other neighborhoods! Wicker Park has easy access to downtown and a younger crowd with tons of cool bars and food.

When to Visit Chicago

The best times to visit Chicago are during summer (June – September) or during a key holiday/event like St. Patrick’s Day. Summer is best for street festivals, better weather, and summer activities like renting a boat or going to the beach. Chicago also goes hard for St. Patrick’s Day (note, it’s always the weekend before the actual holiday) because we die the river green and have bar crawls all over the city.

How to Get Around in Chicago

If you plan on driving in Chicago, we recommend downloading SpotHero for cheaper parking options. Be prepared for lots of traffic jams, full street parking on the weekends, and avoid Lower Wacker – the GPS will get lost!

If you’re up for public transportation, Chicago has one of the best metro’s in the country. The “L,” as we call it, has plenty of trains that run into and out of the city in all directions. And, a few trains that loop around the Chicago Loop as well. You can buy tickets at a metro stop or download the Ventra app.

We’ve also got plenty of Ubers, Lyfts, Divvy bikes, and electric scooters available if weather permits.

Guide to Chicago: Top Things to Do

To make this list pretty thorough, we’re going to skip the fluff and just start listing out places to go and sprinkle in some insider tips along the way. Let’s kick it off with top things to do!

Top Landmarks/Buildings to See

• Snap a pic at the bean: you just kind of have to, it’s Chicago!
• The Chicago Theatre
• The Wrigley Building: not to be confused with the Wrigley stadium, this building is gorgeous (see wedding picture below!)
• Marina Towers
• Buckingham Fountain
• Willis Tower (known to locals as Sears Tower): also famous for the skydeck experience
• John Hancock Building – famous for the tilt experience
• The Ferris wheel at Navy Pier
• Greetings from Chicago mural: we take all our visitors here!
• Amazing skyline views at North Avenue Beach Pier
• Bahai House of Worship: 45 minutes of Chicago but a very cool church and hidden gem

Places to Explore or Tour

• Walk around Millennium Park (it’s the park the Bean sits in)
• Walk the Magnificent Mile
• Do the architecture tour either via boat or kayak – we HIGHLY recommend this! Chicago is famous for its architecture and the tours are very entertaining and worth it! Plus you knock out most of the landmarks listed above.
• Walk around Navy Pier
• Lincoln Park Zoo
• Lincoln Park – specifically South Pond and Peoples Gas Pavillion
• Oz Park – really cute city park in Lincoln Park that has Wizard of Oz statues
• Rent a bike and bike up/down Lakefront Trail
• Walk along the Riverwalk, you can stop for ice cream or wine
• Garfield Park Conservatory

Museums

• Shedd Aquarium
• Art Institute of Chicago (to recreate your Ferris Bueller pic)
• Field Museum
• Museum of Science and Industry
• Adler Planetarium

Comedy

• Second City
• Laugh Factory
• The Den

Seasonal Activities

• Christkindlmarket
• Curling at Kaiser Tiger (need reservation in advance)
• Ice skating at Millennium Park or Maggie Daly Park
• Rent a boat with friends on the lake
• Catch a game of volleyball at North Avenue Beach or Montrose Beach
• Catch a street fest during the summer (there’s almost always 1-2/weekend in summer)
• Wrigley Field – catch a baseball game
• Chicago River during St. Patrick’s Day celebrations (the weekend before St. Patrick’s)

Guide to Chicago: Top Places to Eat (Restaurants)

American

• Au Cheval: no reservations, first-come basis, hard to get in to
• Small Cheval: sister to Au Cheval with many more locations throughout Chicago, great for takeout, lines can get busy but move fast!
• Mott Street
• Lawn Hamburger
• Honey Butter Fried Chicken
• Blue Door Farm Stand

Chicago Staples

• Portillo’s: for the classic Chicago Italian beef staple
• Pizzeria Due for Chicago deep dish, or you can’t go wrong with Lou Malnati’s, Giordanos, or Pequod’s

New American/Fine Dining

• Boka: our favorite Michelin-star new American restaurant (our go-to for celebration dinners)
• Girl and The Goat: really high-end new American (need reservations months in advance if you can get one)
• Alinea: Chicago’s 3-star Michelin restaurant, reservations needed far in advance
• Bloom Plant Based Kitchen: Michelin Bib Gourmand and fully vegan

Asian

Based on the number of restaurants in this category, we clearly have a favorite cuisine:

• Ramen Wasabi: the best ramen we’ve ever had in Chicago – first come, first serve, no reservations so go during early or late dinner hours to avoid crowds
• Ramen Takeya: sister restaurant to Ramen Wasabi, but our friends claim its better
• Mott Street: delicious asian fusion
• MingHin Cuisine: a really good chain all over Chicago for dim sum, Michelin rated
• Lao Sze Chuan: our favorite and go-to for Chinese food (location downtown and in China town)
• MCCB: Michelin star Chinese without the price tag
• Superkhana International: fusion Indian, a little pricier, but the butter chicken calzone was amazing
• Spice Room: our go-to for Indian takeout

Mexican and Latin American

• Taqueria Chingon: the best tacos we’ve ever had in Chicago
• Estrella Negra: top rated Mexican food (mango salsa is so good)
• Big Star: not the most amazing taco’s we’ve had, but a great place to take friends or meet up – it’s about the vibe and the margarita pitchers here. It’s also a chain with multiple locations around Chicago, so always a safe choice.
• Azul: cute brunch spot on the river, great food and booze options

Other

• Time Out Market Chicago: food court for lots of Chicago restaurant options in a popping neighborhood
• Smakosz Restaurant: further to the outskirst of the city, but the best Polish food we’ve had in Chicago
• Pars Cove: a little hidden-gem we found tucked away in Lincoln Park, amazingly priced and delicious persian food
• Park & Field: super fun boozy brunch with outdoor activities

Guide to Chicago: Cafe’s, Desserts, and Snacks

• Bang Bang Pie
• Firecakes Donuts: for amazing cakey or old-fashioned style donuts
• Stan’s Donuts: a classic Chicago place for donuts and coffee
• Alliance Bakery: totally underrated place for amazing pastries and macarons
• Katherine Anne Confections: rich hot chocolate and house-made marshmallows
• The Chocolate Shoppe: Wisconsin ice cream, absolutely phenomenal, worth the drive out. So many vegan options as well!
• La Colombe: great chain around Chicago
• Hexe Coffee Co: coffee and vibes, also good for remote work
• Intelligentsia Coffee: Chicago-founded coffee chain, there’s one right by Millennium park we like to take visitors for a quick pit stop
• Wake-N-Bakery: I’ll let you google it.

Guide to Chicago: Best Bars and Nightlife

River North

• Three Dots and a Dash: speakeasy tropical bar, a bucket-list type place, the line can get crazy
• Miki’s Park: soju, vibes, and a photo booth
• Celeste: really cool bar downtown with different themes to every floor, line can get crazy
• The Hanggee-Uppee: also known as the Hang-Up, this is a “if you know, you know” type of place for very late at night, different decades of music on different floors and dancing
• Howl at the Moon

Wicker Park/Bucktown

• The Up Room: located at the top of a historical building in Wicker Park, this tiny bar (can only hold 15-20 people) gives you rooftop views straight down Milwaukee and into the city. It’s first-come, first-serve so we recommend going right when it opens (5pm).
• The Violet Hour
• Map Room
• Emporium: awesome arcade bar with a few locations
• Big Mini Putt: putt putt bar where they filmed some of Love is Blind
• Fatpour Tap Works: to watch a Michigan football game
• Navigator Taproom: serve yourself taproom with board games and popcorn

Logan Square

• The Owl: for late nights and the jukebox
• Estereo: windows are up in the summer – sweet vibes and drinks!
• The Whistler
• Spilt Milk Tavern
• Emporium: awesome arcade bar with a few locations
• Parson’s Chicken & Fish: for a negroni slushy

We love nightlife in Logan Square, made special by the tamale guy, who goes around selling tamale’s in bars. Watch out for the peppers inside!

Wrigleyville

• Sluggers: bar with batting cages
• Old Crow
• Moe’s Cantina

West Town

• Kaiser Tiger: for curling in the winter, must book in advance
• Beauty Bar: dance the night away

Chicago Top 10

If we had to give you a Chicago guide on the TOP 10 things you HAVE to do (let’s assume its your first trip to Chicago), this is what we’d recommend.

• Millennium Park/Cloud Gate/The Bean
• Chicago Deep Dish Pizza
• Walk the Magnificent Mile
• Architecture Tour
• Comedy show (Second City)
• The Art Institute of Chicago
• Seasonal Activity: curling for winter, renting a boat on the lake for summer
• Bar: Three Dots and a Dash or Up Room
• Restaurant: Eat at one of our favorites (MCCB, Wasabi, Boka, Au Cheval, or Small Cheval)
• Lakeshore Trail: amazing views of the skyline

The Chicago Overrated Guide

Hot takes coming right up! This is our list of tourist traps.

• Eataly: its cool… but did you come to Chicago to visit Italy? Check out the Time Out Market instead.
• The Nutella Cafe: Nutella is delicious, but you can recreate these at home
• Starbucks Reserve Roastery: the line can get egregiously long. If you’re a Starbucks fanatic, it’s probably worth it, if not, skip.
• Quartino Ristorante: a famous Italian restaurant downtown, but as an Italian, my experience was nothing special.
• Kizuki Ramen

The Chicago Underrated Guide (Hidden Gems)

These are places we absolutely love, but are either less-known (don’t make it on those famous Top 10 things to do in Chicago) or farther out from the city.

• Bahai Temple: it’s 45 minutes north of Chicago, which is why it might not make the lists, but super cool if you can make the trip!
• The Chocolate Shoppe: known by the locals as very good ice cream, that’s how you know its good
• The Up Room: most people go to River North for rooftop bars, but we love this one because you see into downtown
• MCCB: we still can’t get over that this is a Michelin-rated restaurant and very reasonable prices
• Greetings from Chicago Mural: there’s never a line to snap an insta pic here!
• Estrella Negra

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