(River North) You'll have plenty of exposure to this place, as it's the wedding venue, but you can also stop by to eat/drink in their main room!
(River North) Where we went on our first dinner date, specifically to Bar Avec's rooftop.
(River North) The group that owns this place also runs Bavette's Bar & Boeuf, Trivoli Tavern, and Au Cheval - all great recs as well!
(River North) A fun choose-your-adventure cocktail bar. Tell the bartender your preferences and see what they whip up!
(River North) Home of Lindsey's favorite espresso martini in the city. You can also find it at RPM Steak or RPM Seafood.
(Gold Coast) Best known for their Christmas decorations and "Christmas in Your Mouth" shots.
(Loop) At the top of our "to try" list - let us know if you make it in!
(Loop) Chicago Athletic Association has a few bars inside (Game Room, Drawing Room, and Cindy's) that are all worth checking out, but Cindy's rooftop is the highlight as you can look out over Millennium Park and the lake.
(Loop) If you're looking for a fun group activity, book a dart board here and play some games.
(Loop) Home of The Bean (legal name: Cloud Gate)! They have an ice skating rink there, and another in the sister park across the bridge, Maggie Daley, if you want a bit of activity.
(Old Town) Chicago's known for its comedy scene so catch a show at this classic venue, or another spot like Laugh Factory.
(Old Town) The city has so many great museums and this is a great one for learning some local history. (other recs: Field Museum, Museum of Science and Industry, Art Institute, and Museum of Contemporary Art)
(Lincoln Park) For those wanting to splurge - this was our first Michelin-starred meal together.
(Logan Square) Junaid's favorite cocktail bar that Lindsey grew to love for its photobooth and patio.
(Logan Square) Cute little spot with a great wine menu!
(Logan Square) A hole-in-the-wall Argentinian steakhouse that's worth going to for its poblano potato amuse bouche alone.
(North Center) If you end up here, let us know because you'll be a block away from our apartment and might as well say hi! Lindsey's go-to cocktail is the Spanish Caravan.
(Lincoln Square) Our go to spot for half priced sushi and $10 martinis until 6pm. It's worth the early dinner!
If you're looking to spend a day exploring downtown Chicago, here's a recommended itinerary!
If you want to experience a "day in the life" in our neck of the woods, here's a recommended itinerary!