• brittany rose

2021 Chicago Travel Guide

Updated: Jul 11

Heading to Chicago soon and looking for where to eat and some of the best things to do and tip and tricks? I've got you covered. This blog post isn't as filled as most of my guides because I stayed with friends and really did this more to catch up with my college besties rather than exploring and doing stuff "for the blog". But I still had so much fun and wanted to share my favorite spots and what's on my bucket list for next time!


I wanted to include a list of all the recommendations I received from all of my fabulous followers on Instagram because they truly know best! Looks like I have a lot more to do on my next trip to Chicago!


** = mentioned 3+ times

  • **London House: rooftop bar, great for the 'gram

  • The Kitchen American Bistro on the river

  • **Hancock Tower Observation Deck

  • Cubs Game day + Wrigleyville

  • **Giordanos

  • Pizza portofino

  • RPM Italian

  • Topo Gigio

  • Cindy's Rooftop Bar: Overlooks the Bean

  • Happy Camper

  • Starbucks Roastery

  • Pequods Pizza

  • **Lou Malnatis: ask for butter crust

  • **Aba

  • **Riverboat Tour

  • Uno

  • Firecakes: for donuts

  • Three Dots and Dash: Tiki Bar

  • **Au Cheval: for the burger

  • Wildberry: breakfast/brunch

  • Eleven City Diner: in Grant Park, don't skip the Challah Bread

  • **Portillos

  • Chicago Pizza Oven Grinders

  • Ginos East

  • Azul Mariscos

  • Ann Sather: amazing cinnamon rolls

  • Nonnina

  • The Smith

  • Summer House

  • Hampton Social

  • Walk the River

  • Beatnik

  • Paradise Park: fun boho pizza vibe

  • Explore Michigan Ave

  • RH 3 Arts Club Cafe

  • IO Godfrey Rooftop Hotel: ask for the rainbow sangria

  • Topolobampo: best night time Mexican

  • **Navy Pier

  • Frontera Grill: best margs and table side guac

  • 3 Dots and a Dash

  • Home Slice

  • **Happy Camper

  • Offshore: for brunch

  • Barcocina: brunch

  • Azul Mariscos: dinner and drinks

  • Utopian Tailgate: rooftop

  • Skydeck at Willis Tower

  • Siena Tavern: for dinner

  • Over Grinder: for pizza bowls

  • **Shore Club

  • Fremont: bottomless mimosas / Sunday funday

  • Restoration Hardware

  • Water tower shopping mall

  • Bandit

  • Federaes: take tequila shot to hit bell with ice cup

  • Emporium: arcdade bar

  • Jo Jos Shakes

  • Etta: tapas food

  • RL Rest

  • Barcocina

  • Replay Lincoln Park: fun, game filled bar

  • Sienna Tavern: best pasta carbonara

  • Nutella Cafe

  • 360 Chicago & get tilt tickets too- it gives you a ticket for a free drink at the sky bar

  • Wake n Bacon

  • Bombabar

  • Machine Engineered Dining

  • Stans Doughnuts

  • Pasta Palazzo

  • Ballpark Pub

  • Murphy's Bleachers

  • Franklin Room: $1.50 oysters from 11:30am-2pm & 5-6:30pm

  • Chicago Public House

  • BombBar: dessert

  • Revival Food Hall

  • Troquet: for happy hour

  • Buckingham Fountain Planetarium Zoo

  • Troquet: $29 entree & 1.5 hours mimosas

  • Bar Cargo: Sat/Sun $25 brunch buffet, $15 bottomless drinks

  • Goddess and Baker: must try the lemon bar

  • Small cheval

  • Pequods

  • The Robey: for brunch or rooftop cocktail

  • Via Carducci: neighborhood Italian

  • Enoteca Roma: neighborhood Italian

  • Spice Room: Indian food

  • Philzcoffee

  • Colectivo Coffee

  • Queen Mary Tavern

  • Birds Nest Bar: wings

  • Kingston Mines: late night music

  • Sienna Tavern: for dinner

  • Cindys Rooftop: drinks and river view

  • donut Vault

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