Starbucks Reserve Roastery
Location: 646 Michigan Ave, Chicago, IL 60611
Note: The largest Starbucks in the world. A place for unique Starbucks coffee, gifts, snacks, and cocktails
Pricing: $-$$$
Goddess and the Baker
Location: 44 E Grand Ave, Chicago, IL 60611
Note: Local chain with pastries and coffee
Pricing: $
Nutella Cafe
Location: 189 Michigan Ave, Chicago, IL 60601
Note: Got a nutella obsession? The first Nutella Cafe in the world here in Chicago. They have coffee, and nutella filled bites.
Pricing: $-$$
Wake N Bakery
Location: 38 E Ontario St, Chicago, IL 60611
Note: For coffee or THC infused baked goods
Pricing: $
Stan's Donuts and Coffee
Location: 535 N Michigan Ave, Chicago, IL 60611
Note: Donut chain that serves coffee. Try the Biscoff Pocket
Pricing: $
Beatrix River North
Location: 671 N St Clair St, Chicago, IL 60611
Note: Coffee house, bakery and restaurant
Pricing: $$
Blue Bottle
Location: 435 N Michigan Ave, Chicago, IL 60611
Pricing: $$
Gotham Bagels
Location: 162 E Superior St Unit B, Chicago, IL 60611
Note: A small chain from Madison, WI that has some of the best New York style bagels and schmears outside of New England. Also a place for breakfast sandwiches
Pricing: $
Goddess and the Baker
Location: 44 E Grand Ave, Chicago, IL 60611
Note: For pastries and coffee
Pricing: $
Beatrix
Location: 519 N Clark St, Chicago, IL 60654
Note: Upscale restaurant that serves coffee, breakfast, lunch, and dinner
Pricing: $$-$$$
Egg Harbor Cafe
Location: 220 E Illinois St, Chicago, IL 60611
Note: Great little breakfast chain with locations in Illinois, Wisconsin, and Georgia for some reason
Pricing: $$
Sunny Side Up
Location: 42 E Superior St, Chicago, IL 60611
Note: Nice little breakfast spot for American classics
Pricing: $$
Egg Tuck
Location: 326 N Michigan Ave, Chicago, IL 60601
Note: Asian-style egg sandwich chain from California
Pricing: $
Do-Rite Donuts and Chicken
Location: 233 E Erie St, Chicago, IL 60611
Note: One of the best donut chains in Chicago. They also have chicken sandwiches (including chicken sandwiches with donuts for a bun). Try the old fashioned donut
Pricing: $
Yolk
Location: 340 N State St, Chicago, IL 60654
Note: Breakfast chain specializing in eggs
Pricing: $$
Nutella Cafe
Location: 189 Michigan Ave, Chicago, IL 60601
Note: Got a nutella obsession? The first Nutella Cafe in the world here in Chicago. They have coffee, and nutella filled bites.
Pricing: $-$$
Wildberry Pancakes and Cafe
Location: 130 E Randolph St, Chicago, IL 60601
Note: They have great pancakes! Get here early or there will be a giant line
Pricing: $$
Eggy's Diner
Location: 333 E Benton Pl Suite 301, Chicago, IL 60601
Note: Diner with breakfast next to a secluded park
Pricing: $$
Ramen-San
Location: 59 W Hubbard St #2, Chicago, IL 60654
Note: For ramen lovers
Pricing: $$
Shake Shack
Location: 66 E Ohio St, Chicago, IL 60611
Note: The New York smashburger chain
Pricing: $
Eataly
Location: 43 E Ohio St, Chicago, IL 60611
Note: Big Italian grocer, importer, and food spot. It has several counters and restaurants inside for the different types of Italian meals and snacks you might want
Pricing: $$-$$$
Star of Siam
Location: 11 E Illinois St # 1, Chicago, IL 60611
Note: Local Thai spot
Pricing: $$
Kyuramen
Location: 6 W Hubbard St, Chicago, IL 60654
Note: Eat ramen in a hexagonal booth! Very instagram friendly. Incidentally, the ramen is also good here
Pricing: $$
Luke's Lobster City Hall
Location: 134 N. LaSalle St., Chicago, IL 60602
Note: Maine-bred seafood shack that highlights superior ingredients. I've eaten here when ALA is in Chicago.
Pricing: $$
Xoco
Location: 65 W Illinois St, Chicago, IL 60654
Note: For Rick Bayless' style of Mexican street food. Make sure you get the churros. Also next to his super fancy place Topolobampo if you have money to burn for super fancy Mexican food
Pricing: $$
Potbelly
Location: 50 E Grand Ave Block 120, Suite 107, Chicago, IL 60610
Note: Local sandwich chain. Like a subway if subway was good
Pricing: $
Nando's
Location: 227 E Ontario St, Chicago, IL 60611
Note: Portuguese chain for peri-peri chicken
Pricing: $$
Bowlicious- The Shops at North Bridge
Location: 520 N Michigan Ave, Chicago, IL 60611
Note: Healthy bowls with fresh ingredients
Pricing: $
Panda Express- The Shops at North Bridge
Location: 520 N Michigan Ave, Chicago, IL 60611
Note: American Chinese
Pricing: $
Chick-fil-A
Location: 500 N Michigan Ave Ste 140, Chicago, IL 60611
Note: Fast food chicken
Pricing: $
Portillo's
Location: 100 W Ontario St, Chicago, IL 60610
Note: Famous Chicago chain for hot dogs, Italian beef, burgers, etc.
Pricing: $
Mr. Beef
Location: 666 N Orleans St, Chicago, IL 60654
Note: Have you seen The Bear? Want to go to the original spot where they filmed the first season? Get your Italian Beef here and pretend to get yelled at by Carmy
Pricing: $
Al's Italian Beef
Location: 548 N Wells St, Chicago, IL 60654
Note: If you want an Italian Beef actual Chicagoans eat at, go here. Their spot in Little Italy is better though
Pricing: $
Pizzeria Uno
Location: 29 E Ohio St, Chicago, IL 60611
Note: The original deep dish pizza. It was invented here.
Pricing: $$-$$$
Giordano's
Location: 730 N Rush St, Chicago, IL 60611
Note: For a different style of deep dish pizza. The crust is breadier and the pizza much saucier
Pricing: $$-$$$
Gino's East
Location: 162 E Superior St, Chicago, IL 60611
Note: Another different style of deep dish pizza. The crust is denser. Still very saucy
Pricing: $$-$$$
Lou Malnati's
Location: 439 N Wells St, Chicago, IL 60654
Note: Yet another different style of deep dish pizza. Favorite of mine. The crust is thinner and crispier and buttery. The pizza is less saucy. Also with gluten free options
Pricing: $$-$$$
Devil Dawgs
Location: 804 N Rush St, Chicago, IL 60611
Note: For a good, classic Chicago Style hot dog
Pricing: $
Billy Goat Tavern
Location: Lower 430 North, Michigan Ave, Chicago, IL 60611
Note: Cheezborger, cheezborger, cheezborger! Visit the place made famous by a 50 year old SNL skit!
Pricing: $
Garrett's Popcorn
Location: 625 Michigan Ave, Chicago, IL 60611
Note: Best popcorn in the city. The caramel and cheese mix is the Chicago standard
Pricing: $
Malort
Location: Any dive bar in the city
Note: Infamous shot you can get about anywhere. Pair it with an old-style for a Chicago handshake. Not for the faint of heart or palate.
Pricing: $
Jibaritos y mas
Location: 3400 W Fullerton Ave, Chicago, IL 60647
Note: For jibaritos which are a puerto rican sandwich with meat between two fried plantains. Unique to Chicago
Pricing: $
Purple Pig
Location: 444 Michigan Ave, Chicago, IL 60611
Note: Modern Mediterranean restaurant with a Bib Gourmand recommendation from the Michelin Guide
Pricing: $$-$$$
Labriola
Location: 535 N Michigan Ave, Chicago, IL 60611
Note: Italian restaurant with pasta and pizza
Pricing: $$-$$$
Monarch and Lion
Location: 302 E Illinois St, Chicago, IL 60611
Note: British restaurant
Pricing: $$$
Girl and the Goat
Location: 809 W. Randolph St., Chicago, IL 69517
Note: Flagship restaurant of celebrity chef and Top Chef winner Stephanie Izard
Pricing: $$$
Rosebud on Rush
Location: 720 N. Rush St., Chicago, IL 60611
Note: Fantastic Italian food, ample portions.
Pricing: $$
The Publican
Location: 837 W. Fulton Mkt., Chicago, IL 60607
Note: Famed for the meats and their breads (which you can get at their bakery or elsewhere on other menus in the city)
Pricing: $$$
Pizza Portofino
Location: 317 N Clark St, Chicago, IL 60654
Note: On the river front- mediterranean style pizza
Pricing: $$
The Smith
Location: 400 N Clark St, Chicago, IL 60654
Note: Casual American brasserie
Pricing: $$
Barrio
Location: 65 W Kinzie St, Chicago, IL 60654
Note: Casual and modern Mexican food
Pricing: $$
Siena Tavern
Location: 51 W Kinzie St, Chicago, IL 60654
Note: Upscale, classic Italian
Pricing: $$$
Quartino
Location: 626 N State St, Chicago, IL 60654
Note: Italian- shared plates style
Pricing: $$
Green Street Smoked Meats
Location: 112 N Green St, Chicago, IL 60607
Note: Central Texas inspired BBQ
Pricing: $$
The Berghoff
Location: 17 W Adams St, Chicago, IL 60603
Note: Long standing pub with German and English food and a good selection of beer.
Pricing: $$
Sunda
Location: 110 W Illinois St, Chicago, IL 60654
Note: Popular space for Southeast Asian fusion and sushi
Pricing: $$$
Ed Debevic's
Location: 159 E Ohio St, Chicago, IL 60611
Note: A diner where the servers are mean in a fun way.
Pricing: $$
Siena Tavern
Location: 51 W Kinzie St, Chicago, IL 60654
Note: Sun-Fri 3-6pm
Quartino
Location: 626 N State St, Chicago, IL 60654
Note: Wed-Thur 4-6pm
The Evie (at the bar)
Location: 537 N Michigan Ave, Chicago, IL 60611
Note: Mon-Fri 3-6pm
The Gwen Hotel
Location: 521 N Rush St, Chicago, IL 60611
Note: Mon-Thur 4-5:30pm
The 101 Bar and Grill
Location: 101 E Erie St, Chicago, IL 60611
Note: Everyday 5-7pm
Hampton Social
Location: 164 E Grand Ave, Chicago, IL 60611
Note: Mon-Fri 4-6pm
Yardbird Table and Bar
Location: 530 N Wabash Ave, Chicago, IL 60654
Note: Mon-Fri 3-6pm
Charlie Martins
Location: 736 N Clark St Chicago, IL 60654
Note: Tues-Sat 5-7pm
The Albert
Location: 228 E Ontario St Fl 1 Chicago, IL 60611
Note: Mon-Sun 4-6pm
Bistro Monadnock
Location: 325 S Federal Chicago, IL 60604
Note: Tue-Sat 2:30-5:30pm
Gus Sip n Dip
Location: 51 W Hubbard St Suite 100, Chicago, IL 60654
Note: Classic styled bar with a large menu of delicious mixed drinks.
Pricing: $$
Three Dots and a Dash
Location: 435 N Clark St, Chicago, IL 60654
Note: Speakeasy throwback tiki bar with fun, inventive, and also shareable drinks. You can get a treasure chest full of rum to share.
Pricing: $$
Flight Club
Location: 111 W Wacker Dr, Chicago, IL 60601
Note: Large bar centered around darts
Pricing: $$
Mother Hubbard's
Location: 5 W Hubbard St, Chicago, IL 60654
Note: Dive-y sports bar that's been in the neighborhood forever
Pricing: $-$$
Fado Irish Pub
Location: 100 W Grand Ave, Chicago, IL 60654
Note: A large Irish pub
Pricing: $-$$
O'Callaghan's
Location: 29 W Hubbard St, Chicago, IL 60654
Note: Cozy neighborhood Irish pub
Pricing: $-$$
Crushed by Giants Brewpub
Location: 600 N Michigan Ave 2nd Floor, Chicago, IL 60611
Note: A new craft brewery
Pricing: $-$$
Headquarters Beercade
Location: 213 W Institute Pl, Chicago, IL 60610
Note: A barcade with retro arcade games and pinball machines
Pricing: $-$$
Guinness
Location: 901 W Kinzie St, Chicago, IL 60607
Note: Out of the neighborhood, but Guinness has a brewery in Chicago and they don't just brew Guinness. It's quite large and very new
Pricing: $$
Riverwalk
Location: Chicago Riverwalk, Chicago, IL
Note: Take a stroll on the river walk! The city has put a lot of work into making the riverwalk extremely pleasant and lively. There are a number of restaurants and bars on the river or go rent a kayak or an electric boat to explore the river more
Chicago Architecture Center River Cruise
Location: Chicago Architecture Center, 111 E Wacker Dr, Chicago, IL 60601
Note: Take a sail down the Chicago River with a docent who will tell you all about the famous buildings that populate the skyline. There are other companies that have river cruises, but this is the best and most architecture focused one.
Millennium Park
Location: Millennium Park, 201 E Randolph St, Chicago, IL 60602
Note: See the Bean! Take in a concert at Pritzker pavilion! Stroll around Lurie Garden!
Art Institute of Chicago
Location: 111 S Michigan Ave, Chicago, IL 60603
Note: The best museum in Chicago. The largest impressionist painting collection outside of France. See classics like A Sunday on La Grande Jatte (the dots one), American Gothic (the farmer and his daughter one), Nighthawks (the one with the diner), or other works by Andy Warhol, Pablo Picasso, El Greco, Claude Monet, Mary Cassatt
Museum of Contemporary Art
Location: 220 E Chicago Ave, Chicago, IL 60611
Note: The modern art museum of Chicago. If you want to be challenged by art in a beautiful, modern setting, head here.
Navy Pier
Location: 600 E Grand Ave, Chicago, IL 60611
Note: A lively pier with shops, restaurants, and lake cruises. Home of the giant ferris wheel and the Chicago Shakespeare Theater
Harold Washington Library Center
Location: 400 S State St, Chicago, IL 60605
Note: The main library of the Chicago Public Library. Check out the special collections exhibits and the winter garden on the 9th floor.
Chicago Cultural Center
Location: 78 E Washington St, Chicago, IL 60602
Note: The former main library of the Chicago Public Library is now a free cultural center with rotating art exhibits and performances. Check out the Tiffany Dome
Willis Tower
Location: 233 S Wacker Dr, Chicago, IL 60606
Note: Once the tallest skyscraper in the world, go up to the sky deck, a glass box jutting out over the city with views straight down 100 stories. Tip: People in the city still usually refer to it as its previous name Sears Tower. So if people are confused as to what you're talking about, call it Sears Tower
John Hancock Building
Location: 875 N Michigan Ave, Chicago, IL 60611
Note: A giant building named after the man with the biggest signature on the declaration of independence. There is an observation deck called 360 Chicago and see if you can endure the Tilt where you place your body against the glass while it tilts the whole floor down.
Harry Potter Shop Chicago
Location: 676 Michigan Ave, Chicago, IL 60611
Note: The Harry Potter store! Get a wand or some butterbeer
American Writers Museum
Location: 180 North Michigan Ave, Chicago, IL 60601
Note: A museum devoted to American writers
McCormick Bridgehouse and River Museum
Location: 99 Chicago Riverwalk, Chicago, IL 60601
Note: A museum on the Chicago river devoted to the river and city's movable bridges
Chicago Fed Money Museum
Location: 230 S LaSalle St, Chicago, IL 60604
Note: Free museum devoted to money! (Something we could all use a little more of)
Driehaus Museum
Location: 50 E Erie St, Chicago, IL 60611
Note: A gilded age mansion turned into a museum. Gape at the incredibly beautiful house and furnishings of houses like in that one show on HBO.
International Museum of Surgical Science
Location: 1524 N Lake Shore Dr, Chicago, IL 60610
Note: A museum devoted to surgery housed in a former gilded age mansion that was then turned into a college of surgery before becoming a museum devoted to the profession
Chicago Shakespeare Theatre
Location: 800 E Grand Ave, Chicago, IL 60611
Note: Shakespeare Theatre on Navy Pier modeled after Shakespeare's Original Globe Theatre. Will be playing the Merry Wives of Windsor
Goodman Theatre
Location: 170 N Dearborn St, Chicago, IL 60601
Note: August Wilson's play Ma Rainey's Black Bottom will be playing
Steppenwolf Theatre
Location: 1650 N Halsted St, Chicago, IL 60614
Note: The legendary Chicago theatre started by Gary Sinise will be playing Windfall
CIBC Theatre
Location: 18 W Monroe St, Chicago, IL 60603
Note: Will be playing hamilton
Chicago Symphony Orchestra
Location: 220 S Michigan Ave, Chicago, IL 60604
Note: Evgeny Kissin with the CSO, April 16, 2026
Second City
Location: 1616 N. Wells St., Chicago, IL 60614
Note: The Second City opened its doors on a snowy Chicago night in December of 1959, and a comedy revolution began.
White Sox Game
Location: 333 W 35th St, Chicago, IL 60616
Note: Home games vs. the Tampa Bay Rays Tuesday 4/14-Thursday 4/16
Wrigley Field
Location: 1060 W Addison St, Chicago, IL 60613
Note: The cubs will not be playing, but the famous park is a landmark and surrounded by bars and restaurants in a lively part of the city
Chicago Greeter Tours
Location: https://www.chicagogreeter.com/
Note: Free neighborhood tours with a local guide. Riverwalk and Loop tours are nearby
Buddy Guy's Legends
Location: 700 S Wabash Ave, Chicago, IL 60605
Note: Blues club with frequent shows from some of the world's most talented musicians.
Kingston Mines
Location: 2548 N Halsted St, Chicago, IL 60614
Note: Oldest continuously operating blues club in Chicago.
Newberry Library
Location: 60 W Walton St, Chicago, IL 60610
Note: Historic cultural institution founded in 1887. As they describe, 27.5 miles of shelf space and 600 years of human history.
Northerly Island
Location: 1521 S Linn White Dr, Chicago, IL 60605
Note: A manmade peninsula and former airport now restored to a nature preserve
Montrose Point Bird Sanctuary
Location: 4400 N Lake Shore Dr, Chicago, IL 60640
Note: This 15 acre sancuary includes prarie, savanna and woodland. It is Illinois's busiest birding spot.
Garfield Park Conservatory
Location: 300 N Central Park Ave, Chicago, IL 60624
Note: One of the largest greenhouse conservatories in the United States.
Jackson Park
Location: 6401 S Stony Island Ave, Chicago, IL 60637
Note: A large urban park featuring lagoons and a Japanese garden. It is surrounnded by remnants of 1893 World's Columbian Exposition and the future sight of Barack Obama Presidential Center
The 606 / Bloomingdale Trail
Location: 1800 N Ashland Ave, Chicago, IL 60622 to 1800 N Ridgeway Ave, Chicago, IL 60647
Note: An above grade railway turned greenway connects several parks.
The Wild Mile
Location: 905 W Eastman Street, Chicago, IL
Note: A floating park part of Chicago's attempts to make the Chicago river more livable for all of its residents regardless of how many legs, fins, beaks or tails they may have.