We love living in Chicago! If you plan to spend a few days with us, here are some of our favorite places. And please don't hesitate to ask us for more recs!

West Loop - Jill's favorite neighborhood

The Hoxton Hotel - Whether you're grabbing a drink at the lobby bar (like we did on date #5) or dining at Cira (bottom floor) or Cabra (rooftop), this place is always a good time.

Oakville Grill & Cellar - Where Napa Valley meets Chicago's Fulton Market District. Delicious!

Lyra - Greek food. Loud. Crazy. Sparklers on your birthday (or you could pretend it's your birthday)!

Grapes and Grains - Piano bar. Wine. So much fun!

West Town/Bucktown

Maxwells Trading - Just opened in 2024, we've had some great meals here (Asian, West Coast and Mediterranean small plates) together and separately. A can't miss - but also books up quickly!

Big Star - Tacos + Margs. Maybe a Texas two-step class will also be in session.

Downtown/River North

Avli on the Park - Several locations throughout the city, but their downtown restaurant was where Jill's last birthday was held. Amazing Greek food, incredible vibes.

Tanta - Peruvian. Small plates. Great rooftop.

Tre Dita - Italian restaurant at The St. Regis. Incredible food and views. Incredibly hard to get a reservation, but worth trying!

The Bassment - The least clubby club (technical term), with great music.

Lincoln Park

Summer House Santa Monica - Airy California vibe. Great for brunch. Cookies the size of your head.

Willow Room - Awesome patio. Great drinks.

Old Town - Jill's neighborhood (until she moved in with Wyatt!)

The J. Parker - Restaurant at the top of the Lincoln Hotel, site of our first Valentine's Day (and Jill's farewell party back in 2013). Amazing views of Lake Michigan.

The Vig - Upscale sports bar. West Loop location too!

Topo Gigio - Classic Italian. Great patio

Humboldt Park - Wyatt's neighborhood

Rootstock Wine & Beer Bar - Very cute. Very cozy. Very close to Wyatt's.

The Hi-Lo: Fun to grab drinks. Also close to Wyatt's!

Besides eating and drinking, it's a rite of passage to take the Architecture Boat Tour. Otherwise just walk around, basking in what many people consider to be one of the best cities in the U.S. - at least May - September :)