My List: Chicago Beyond Navy Pier and Uno’s | 2nd Edition

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Crossrhodes in Evanston (I know, I know, it’s not the city)

This is an updated post from this original post. Definitely google XYZ before heading out to make sure it’s still open. An “always being updated” updated list can be found on the Lists Page > Life of Yes℠ Resources > “Getting Out There” tab.

Disclaimer: as of July 2025, I no longer live in Chicago, so there is oodles of new’ness I don’t know about! Check the Resources section for most up to date loves by people who actually live in 312 / 773.

I love getting asked about my dear (ex-)city! And people do, often.

So in Saya-Fashion, for ease and efficiency and because who doesn’t love a list?!, I’ve compiled some of my recommendations. I’ve made it a point to explore and share Chicago beyond Michigan Avenue, the Bean and the Cubs— lovely options but there’s so much more. All below are in the city except when noted by a following suburb name. For all the grief city-dwellers give suburbanites, Chicago actually has some pretty awesome neighbors.

This list isn’t anywhere near comprehensive — my brain started to hurt and I had to stop — and of course things are always opening and closing. If you have any additions or “That place doesn’t exist anymore!” insight, let me know in the comments. I’ll update as applicable.

Some of the items are recommendations via Cheese-Its and I haven’t yet experienced them, some of the items are tried and tested and thumbs up’ed by me.

If a link isn’t provided, give it a Google!

Bookmark, share with people going to visit, come back and comment after you experience something amazing.

Enjoy exploring the best big US city! (In my non-humble opinion…)

RESOURCES

TRANSPORTATION

Do not rent a car for your Chicago trip. If you’re driving your own car, park it in a neighborhood outside of downtown where you can leave it for the duration of your trip, or even a suburb, and then train or ride share it into the city; make sure you check signs! Not every lot allows overnight parking and if you park on the street, you need to know the street rules. City parking, at hotels and in garages, is horribly expensive. And you 100% don’t need a car and will probably find it annoying. If you have to drive, use apps like ParkWhiz to find the cheapest options.

Chicago has an amazing public transit system — the CTA, Pace, and Metra — comprised of trains and busses that run frequently and at most hours. Besides getting you from A to B, it’s also a fun and inexpensive way to see the city and surrounding areas. See “Activities” for suggested routes to take if you want to check out the city via public transit.

Both airports have trains to downtown and are much cheaper than taking a shuttle or cab or the like. Plus, traffic is often a nightmare; bypassing all the stopped cars while you’re on the El is the best!

Chicago is also extremely walkable and bikeable. Use Google Maps to map out routes by whatever transit method you’re using.

Bike-share: Divvy Bikes — hop on and off these bright-blue, easy to ride bikes all over the city. Get a 24-hour pass. Unlimited rides but be sure to re-dock within the 30 minute time period or you’ll be charged. Download the Divvy app to help you locate docks and bikes, as well as track how much time you have left. With its flatness and bike-lanes, Chicago is a wonderful city for cycling (try Dearborn St, Kinzie St, Jackson Boulevard, and any of the paths). Be careful though — there are definitely streets where you should NOT bike.

The Water Taxi is a fun way to move around downtown and a cheaper version of the boat tours below (though that’s money well spent).

LODGING

All have good walkability scores and are accessible via public transit and are in cab meccas.

Downtown hotels

In the city but not downtown hotels

Neighborhoods for Airbnb’ing if you want to be in the heart of the city

  • West Loop
  • South Loop
  • River North
  • River West
  • The Loop
  • Streeterville

Neighborhoods for Airbnb’ing if you want to be in the city but more in a neighborhood

  • Roscoe Village
  • Wicker Park
  • Bucktown
  • Old Town
  • Lincoln Square
  • Lincoln Park
  • Andersonville

FOOD

Ambiance / Experience

  • Gene’s Sausage Shop
  • Gospel Brunch at House of Blues
  • Weiner Circle at 2 AM (don’t ask for a chocolate milkshake; or do…)

Asian

  • Aroy
  • Joy Yee’s
  • Kai Sushi
  • Qiao Lin Hotpot
  • Sun Wah BBQ (pre-order the duck)
  • Tuk Tuk Thai Isan

Bagels

  • Gotham
  • Helfeld’s
  • Kaufman’s Bagel & Delicatessen (Skokie)
  • Once Upon a Bagel (Highland Park)
  • Tilly

BBQ

Burgers

  • Au Cheval
  • Billy Goat Tavern
  • Gordon Ramsay Burger
  • Small Cheval (the wait is much shorter than at Au Cheval; the original one is in Wicker Park)

Colombian

  • Mekatos

Culinary School Restaurants

  • Parrot Cage
  • Sikia Restaurant

Deli

  • Bari Foods
  • Helfeld’s
  • JP Graziano
  • Manny’s
  • North Buena Deli

Diners

  • Eleven City Diner
  • Lou Mitchell’s
  • Pick Me Up Cafe
  • White Palace Grill

Donuts

  • Beacon Doughnuts
  • Do-Rite Donuts
  • Firecakes
  • Stan’s
  • The Donut Vault
  • Voodoo

Eclectic

  • Celeste
  • Duck Duck Goat
  • Lula Cafe
  • Medici
  • The Purple Pig
  • Txa Txa Club (fixed-price communal supper)

Ethiopian

  • Demera
  • Ethiopian Diamond

Filipino

  • Kasama

Fried Chicken

  • Crisp
  • Gus’ World Famous Fried Chicken
  • Harold’s Chicken (there are tons; google to see which one folks recommend)
  • Honey Butter Fried Chicken
  • Roost Chicken & Biscuits

Greek

  • Athena Greek Restaurant
  • Cross-Rhodes (Evanston; you MUST get the Greek fries)
  • Greek Islands

Hot Dogs

  • Portillo’s

Ice Cream

  • Jeni’s
  • Margie’s
  • Scooter’s
  • Vaca

Indian

  • Anywhere on Devon Street that has a lunch buffet
  • Ghareeb Nawaz
  • India House
  • Thattu (owned by a Cheese-It!)
  • Tiffin

Italian

  • Alla Vita
  • Monteverde Restaurant & Pastificio
  • Quartino Ristorante

Italian Ice

  • Mario’s

Markets & Variety

  • Aster Hall
  • Chicago French Market
  • Eataly
  • From Here On
  • Green City Market

Mexican

  • Frontera
  • La Luna
  • Las Carnitas Uruapan
  • Nuevo León Restaurant
  • QuesaBirria Jalisco Pilsen
  • Topolobampo
  • XOCO

Pizza (deep-dish)

  • Art of Pizza
  • Bartoli’s
  • Chicago Pizza and Oven Grinders
  • Pequod’s

Pizza (thin-crust)

  • Coalfire
  • Dante’s
  • Italian Fiesta
  • Middlebrow
  • Phil’s Pizza D’Oro
  • Pizza Rustica
  • Salerno’s Pizza
  • Spacca Napoli
  • Vito and Nick’s

Southern

  • Big Jones

Steakhouses

  • Bavette’s Bar & Boeuf
  • Chicago Chop House
  • Erie Street Cafe
  • Fleming’s
  • Gene & Georgetti
  • Gibsons
  • Tango Sur

Sweet Treats Beyond Donuts

  • Bang Bang Pie Shop
  • Cadinho Bakery and Cafe
  • Delsur
  • First Slice
  • Hoosier Mama
  • Levain Bakery
  • Lost Larson
  • Mindy’s
  • Sugar Moon
  • West Town Bakery

Tacos

  • Big Star
  • La Chaparrita Taqueria
  • Velvet Taco

Tea Time

  • High Tea at The Drake
  • Soho House

Trendy / Reservation-Worthy

  • Avec
  • Burl (Evanston)
  • Chef’s Special
  • Chez Poulet
  • Giant
  • Girl & the Goat
  • Kie-Gol-Lanee
  • Mirra
  • Next
  • Pompette
  • Publican
  • QXY Dumplings
  • RL
  • Virtue

Vegetarian / Vegan

  • Beacon Doughnuts
  • Blue Sushi Sake Grill
  • Chicago Diner
  • Kale My Name
  • Penelope’s Vegan Taqueria
  • Planta
  • Soul Vegetarian East
  • Urban Vegan
  • Vaca
  • West Town Bakery

Views

  • Cindy’s
  • LH Rooftop
  • The Robey

DRINK

Coffeehouses —

  • Kibbitznest
  • Collectivo
  • Star Lounge
  • Wormhole
  • Kopi
  • Hexe
  • Cafe Jumping Bean
  • Cafe Mustache
  • Jackalope
  • Bridgeport Coffeehouse
  • Gaslight Coffee
  • Perfect Cup
  • La Columbe
  • Osmium
  • Sawada Coffee
  • Starbucks Reserve Roastery (largest Starbucks in the world)

Tasting Rooms/Breweries—

  • Bitter Pops
  • Beermiscuous
  • Revolution Brewing
  • Begyle Brewing
  • District Brew Yards
  • Pilot Project

Bars—

  • The Map Room
  • Simone’s
  • Globe Pub
  • Hopleaf
  • Three Dots and a Dash
  • Maria’s Packaged Goods & Community Bar
  • Babe’s and Whiskey Girl (women’s sports bars)

ACTIVITIES

Physical—

  • The 606: train tracks converted into a 2.7-mile elevated walking, running, and biking trail path that snakes through multiple neighborhoods
  • Chicago River Canoe & Kayak
  • Dance Dance Party Party
  • Trail paths (the Lakefront path, Burnham Greenway Trail, Greenbay Trail Path, North Shore Channel Trail, the 606)
  • Whirlyball
  • Chicago Boat Company
  • Critical Mass: group bike ride
  • Chicago Girls Who Walk

Theater—

  • Steppenwolf
  • Lookingglass
  • Chicago Shakespeare Theater
  • The Den
  • Broadway in Chicago
  • Steep
  • Timeline

Museums—

  • Chicago Historical Society
  • Adler Planetarium
  • Shedd Aquarium
  • Peggy Notebaert Nature Museum
  • Smart Museum of Art
  • Chicago Architecture Center
  • Glessner House
  • National Public Housing Museum (check out their event schedule!)
  • Museum of Science & Industry
  • Museum of Contemporary Art
  • Art Institute
  • National Museum of Mexican Art
  • American Writer’s Museum
  • Richard H. Driehaus Museum
  • Pullman Museum
  • DuSable Museum
  • Obama Presidential Center
  • Illinois Holocaust Museum & Education Center (Skokie)
  • Field Museum
  • McCormick Bridgehouse & Chicago River Museum
  • Museum of Illusions

Music—

  • Old Town School of Folk Music
  • Thalia Hall
  • Lincoln Hall
  • Salt Shed
  • City Winery
  • Millennium Park
  • The Hideout
  • Schuba’s
  • Beat Kitchen
  • SoFar Sounds
  • Martyr’s
  • The Green Mill
  • Howl At the Moon
  • Redhead Piano Bar
  • Ravinia (Highland Park)
  • SPACE (Evanston)

Classes—

Potpourri—

  • Lincoln Park Zoo: the world’s largest free zoo
  • Chicago Public Library, Harold Washington branch
  • Chicago Tool Library
  • Catcade: “a non-profit, arcade-themed cat rescue, lounge, and our version of a cat café”
  • Chicago Magic Lounge
  • 2nd Friday Gallery Nights
  • Movies: Music Box Theater
  • Farmer’s Markets (Green City Market, Logan Square)
  • Street Festivals
  • B’hai Temple (Wilmette)
  • Colleges: Northwestern (Evanston) & University of Chicago (there are many more than this but these are my favorite to meander)
  • So many movies and TV shows were shot/are shot in Chicago, with many locations very easy to get to or far but a fun adventure to get to —
    • Home Alone
    • The Dark Knight
    • High Fidelity
    • Untouchables
    • Adventures in Babysitting
    • Hoop Dreams
    • Candyman
    • Barbershop
    • While You Were Sleeping
    • The Bear
    • ER
    • The Good Wife
    • Breakfast Club
    • Sixteen Candles
    • Ferris Bueller’s Day Off
    • Chicago PD, Chicago Fire, Chicago Med
    • Blues Brothers

Parks/Outdoors—

Tours—

Storytelling | Presentations | Live Lit—

  • Pecha Kucha
  • The Moth
  • Lectures On Tap
  • Creative Mornings
  • Chicago Humanities
  • Mortified
  • Interview Show
  • Louder Than a Mom
  • Paper Machete: free variety show every Saturday at 3pm in an iconic Chicago music venue, the Green Mill
  • Write Club

Comedy—

  • Improvised Shakespeare
  • Free Wednesday show at io (improv olympic)
  • Second City
  • The Annoyance Theater
  • Comedy Sportz

Spas—

  • King Spa
  • Chicago Bath House
  • Aire Ancient Baths

Events (once year events) —

  • Pride Parade
  • Air & Water Show
  • Bud Billiken Parade
  • Chiditarod
  • Bike the Drive
  • Open House Chicago

Sports—

  • Windy City Rollers (roller derby)
  • Chicago Sky (WNBA)
  • Chicago Stars
  • Chicago Fire (soccer)
  • Chicago Hounds (rugby)
  • Chicago Bulls (NBA)
  • Chicago Cubs and White Sox (MLB)
  • Chicago Blackhawks (NHL)
  • Chicago Bears (NFL)

Games—

  • Guthrie’s
  • Bonus Round Game Cafe
  • Snakes & Lattes
  • Emporium
  • Game Night Out

Shopping—

  • Randolph Street Market
  • Areas: Wholesale district on Clark St (Wilson to Sunnyside), Wicker Park/Bucktown (boutiques/independent stores, Milwaukee/North/Damen), Andersonville (vintage, independent stores), Michigan Avenue (Chicago’s main shopping drag, with all your well-known stores)
  • Household/Furniture: Nadeau, Primitive, Salvage One
  • Merz Apothecary
  • Gifts / Chicago / General Store: Midwest Nice, Raygun, Enjoy, Transit Tees, Neighborly, Judy Maxwell Home, You Are Beautiful
  • Bookstores: Zora’s Place (Evanston), Open Books, Myopic Books, Newberry Bookshop, Passages, City Lit, Book Cellar, Women & Children First, Barnes & Noble in Wicker Park (the most beautiful B&N I’ve ever seen, in an old bank)

Touristy stuff that’s fun—

  • FlyOver: “Our exhilarating immersive journeys connect you with our planet like never before. Soar over iconic locations, dive into authentic stories and lose yourself to an adventure unlike any other.”
  • 360 Chicago: “Experience the impressive panoramic views of the Chicago skyline and Lake Michigan from 1,030 feet above the famed Magnificent Mile at the 360 CHICAGO Observation Deck.”
  • Skydeck Chicago at the Sears Tower
  • The Bean
  • Millenium Park
  • The Riverwalk
  • Buckingham Fountain
  • The Chicago Theatre marquee: take a photo

Volunteering—

  • Chicago Cares
  • My Block My Hood My City
  • Southside Blooms
  • Night Ministry
  • Liberation Library
  • One Brick
  • Open Books
  • Open Heart Magic
  • Animals: One Tail at A Time, PAWS, Anti-Cruelty, Chicago Animal Care and Control
  • Refugee One

EXPLORE

Ride public transit—

  • Brown Line from downtown all the way to the end of the line at Kimball; all above ground
  • Evanston Express from downtown to Linden (only runs weekdays rush-hour); all above ground
  • Metra Union Pacific North line from downtown to Highland Park
  • #22 Clark St bus from downtown to Andersenville (Bryn Mawr stop)
  • Water Taxi from Navy Pier to Chinatown

Meander by foot—

  • Lincoln Square
  • Pilsen
  • Andersonville
  • Lincoln Park
  • Wicker Park
  • West Loop
  • Michigan Avenue
  • Old Town

Trips to the suburbs—

  • Evanston: Northwestern, bustling downtown, eateries, the apartment where I was born – where I got my first concussion – where I stole a Barbie Doll — aka my childhood home
  • Naperville: bustling downtown, eateries
  • Oak Park: Frank Lloyd Wright houses
  • If you like ogling rich people homes, the North Shore is suburb after suburb of beautiful homes, From Evanston to Lake Forest. If you have a car, drive Sheridan road. You can also bike and Metra it (this line takes you from Downtown up to Lake Forest; it’s a really comfy relaxing ride).

TIPS

  • Once you learn about the grid system, it’s easy to get around. We talk logically when giving directions, like “go two blocks north” and “head to 3200 N Clark” which you’ll know to be south of you, since you’re at 4800 N Clark
  • You’ll probably get a ton of downtown and north side recommendations (*cough* my list) — there’s a wonderful city South and West as well
  • You’re in a city where you don’t know anyone — sign up for an open mic! Sing, stand-up, tell a story. Why not?!?
  • For last minute and/or discount tickets: HotTix, TodayTix Chicago
  • If you are a Chicago resident with an adult Chicago Public Library card in good standing, you can reserve digital museum passes through Explore More Illinois

What would you add?!

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