Breakfast:

Leonidas Cafe (French cafe, chocolate shop)

Beacon Donuts (Instagramable location, Vegan)

Golden Apple (American)

Goddess & the Baker (Casual cafe)

Ann Sather (Great cinnamon roll)

Brunch:

The River (Drag Brunch)

Roscoe’s (Drag Brunch)

Nookies on Wells (American)

The Gundis Kurdish Kitchen (Kurdish breakfast, baklava crepes)

Bub City (BBQ)

Lunch/Dinner:

El Nuevo Mexican Restaurant (Our favorite in Chicago)

Bistronomique (French)

Avli River North (Greek)

Havana Grill (Cuban)

Beatnik on the River (Chicago River views)

Pizzeria Portofino (Chicago River views)

Bungalow by Middle Brow (Brewery with house made sourdough pizzas)

Cocina Tarascas (JUMBO margaritas)

Nobu (Sushi)

Sushi Rotary + (Conveyor belt sushi)

Figo Wine Bar (Tapas, wine pairings)

Torchio Pasta Bar (Best pasta in Chicago)

Medi (Mediterranean)

Gaijin (Japanese, Okonamiyaki)

Beat Kitchen (Live music, hipster vibes, vegan options)

Demera (Ethiopian)

Quartino’s (Shared-plate pasta)

Tiny Tapp Cafe (On the Chicago River)

Au Cheval (Great burger, but long wait and no reservations)

Small Cheval (Fast casual version of Au Cheval)

Koi Sushi (All you can eat sushi)

Sushi Para II (All you can eat sushi)

Sushi San (Modern sushi)

Ramen San (Modern ramen)

Moti (Modern Indian)

Old Jerusalem (Mediterranean)

Green Tea Japanese Restaurant (Desta’s favorite sushi)

Sultan’s Market (Fast/Takeout mediterranean)

Crisp (Award Winning Fried Chicken)

Taza Cafe (Mediterranean, Best falafel)

Chicago-Style Hot Dogs, Deep Dish Pizza, Italian Beef:

Devil Dawgs (Chicago Dog)

Portillo’s (Chicago Dog, Beef & Sausage “Combo” Dipped, Burger)

Peaquod’s (Pizza)

Lou Malnati’s (Pizza)

Giordano’s (Pizza)

Mr. Beef (Beef & Sausage “Combo” Dipped / "The Bear" filming location)

Late Night Food:

Taco Burrito Express

Windy City Gyros

Blues Bars:

Kingston Mines

Blue

Bars:

Sparrow (Cocktail bar)

Arbella (Cocktail bar)

Alive One (Music bar)

Old Town Pour House (American bar)

Glunz Tavern (German brewpub)

Prost (German brewpub)

Celeste (Cocktail Bar)

Disco (Dancing bar above Celeste)

Miki’s (K-Pop bar, free photo booth)

Hopsmith (Bar & Grill)

The Green Mill (Cocktail Lounge)

The Lodge (Open Late)

Centennial (Casual bar)

Breweries:

Rooftops:

Clubs:

LGBTQ+ Bars:

Beaches:

Activities / Sightseeing:

Wendella (City architecture tour by boat)

Bike the lakefront trail (Divvy bike rentals throughout the city / e-bike recommended)

Oak St luxury shopping

Wrigley Field (Cubs baseball games)

Sears Tower (Willis Tower)

Hancock Tower

Route 66 Start (Adams St. & Michigan Ave)

Second City

Chinatown

Six Flags Great America (Amusement Park)

Bahá'í House of Worship

Medieval Times

Bristol Renaissance Fair

Time Out Market