If I were you visiting the city and staying in River North, this would be my agenda! Friday: Check into hotel, settle, and get dinner near your hotel in River North at Zarella, Ema, or Gilt Bar. Grab either a pre or post dinner drink at Gus’ Sip and Dip for tasty and creative cocktails. Saturday: Leisurely morning. Grab coffee at Cafe Umbria or Blue Bottle Coffee (near hotels in river north) and walk along the river walk. (Stairs are on the south end of the bridges off of LaSalle, Clark, and Dearborn St. Grab lunch at Pizzeria Portofino or something quick like Sweetgreen before you do the Architecture Boat Tour early afternoon (ideally catching the air and water show from here). Head back to the hotel to get ready. Grab a rooftop cocktail around 5pm at London House, IO Godfrey, Roof on the WIT, or Raised. Meet us at Boss Bar at 7pm to party. Sunday: If you have the energy for it after our epic party, head to the lakefront (Oak Street Beach or North Ave Beach) to see Lake Michigan!
Chicago’s annual Air and Water Show takes place August 15th and 16th! That means the lakefront is going to be pretty busy, however it’s a really cool event to go to. Make time to go Saturday before the party or Sunday before you leave! Rooftop bar recommendations below too
Make sure to check if reservations are needed or get there early since it’s air and water show weekend! London House AIRE Raised Cindy’s Streeterville Social Terrace 16 IO Godfrey The J. Parker
The BEST thing to do in the summer! Wendella Tour: https://wendellaboats.com/pages/schedule-tickets?gad_source=1&gad_campaignid=16390982594&gclid=CjwKCAjwuanRBhBSEiwAY5y6V14fCO1oaq9Hgszgg_doBcW5zH0sJ9Lv_fScDrh3wO5M4uHshYEtEhoCPOkQAvD_BwE Tours & Boats: https://toursandboats.com/?utm_source=google&utm_medium=organic&utm_campaign=gbl Another company: https://architecturetourchicago.com/
River North (where Boss Bar is): Zarella RPM Italian Lil Ba Ba Reeba Sushi San Sunda Matilda Beatrix Ema Chicago Cut (really nice steakhouse) If you want recommendations for a different neighborhood, I have PLENTY that are amazing. Just text me!