Places to Stay:
Langham- most people would say this is the nicest hotel in Chicago. 5-star hotel located in downtown Chicago.
Soho House- member-exclusive club. If you stay here, you have access to all the amenities that club members do. The gym & pool are top-notch.
The Hoxton- European Hotel located in Fulton Market
London House- great location on the Riverwalk and well-priced. Typically on hotel tonight!
 
Places to Eat:
Piccolo Sogno- great Italian spot with a fun patio near Fulton market. My favorite Italian restaurant in Chicago.
Ralph Lauren- Ask for Peter as your waiter! He's a gem. This is always a great restaurant to go for date night or for a ladies lunch. The design is loungey- think leather and navys with great gallery walls. If its a good weather day, request the patio! Dont skip on the fries. The burger and vegetable chop salad are delish!
Bavette's- this restaurant, Ciccio Mio, and Gilt Bar are all owned by the same group. Plus, they are located all on the same block. Most locals would say this is their favorite restaurant in Chicago, and I agree. The food is spectacular and the interior design is very sexy. Bavettes is a classic steak house. If you can't get a reservation, try to walk in and sit at the bar.
Ciccio Mio - the newest addition to the Hogsalt restaurant group. This Italian spot is the new hot spot in Chicago. The food is out of this world. They offer gluten-free pasta, and their lamb ragu is a must-order.
Cabra- The rooftop on the top of the Hoxton hotel.
Fronterra - Rick Bayless Mexican restaurant. Great Mexican food for the midwest!
Viagra Triangle- Gibsons, Tavern on Rush, Maple and Ash, Lux Bar
Galit- a middle eastern restaurant in lincoln park. Make sure to get the brisket hummus.
Aba- owned by the lettuce entertain you group. Greek food menu with a great rooftop in Fulton market
RPM Seafood- the lettuce entertain you group's newest restaurant. Located on the Riverwalk. Great menu and wine list.
Momotaro- easily Chicago's best sushi located in Fulton market.
Au Cheval - easily the best burger in Chicago. Au Cheval has smaller chains, Small Cheval that solely serve burgers. Au Cheval in Fulton has more on the menu. My favorite is to go late-night, enjoy a burger and bottle of wine. They do not take reservations, so plan accordingly. I have a gluten allergy, and they will wrap your burger in lettuce- it's truly fantastic!
Mott St- in second place for the best burger in Chicago. The burger at Mott St has an Asian flair.
Boka- A classic restaurant in Lincoln Park.
Topo Gigio- neighborhood Italian restaurant on wells street. No reservations. A classic Chicago restaurant.
Restoration Hardware - 3H Café. A unique Café in the center of the restoration hardware store located in the gold coast.
 
Tasting Menus:
Next- tasting menu that is constantly changing. located in Fulton market 
Alinea- Lincoln park tasting menu. Known for their "create your [table] dessert"
Mako- sushi spot in Fulton market. Fantastic sashimi. 
Oriole- located in Fulton market in a fun warehouse restuarant.
Ever-newest tasting menu to the city.
Topolobambo - high end Mexican food by chef Rick Bayless located inside Fronterra. Try to go when they are featuring their mole tasting menu. This is Evan and I's favorite restaurant in the city!
Aviary- tasting menu for cocktails
 
 
First Timer Visitor Check List:
Have a drink on the rooftop at the London House
Walk the Riverwalk and pop into city winery
Stroll through Grant Park and then take a picture at the Bean
Head up to the rooftop at the Chicago Athletic Club- Cindys Rooftop, for a great view of the Bean!
Catch a cups game at Wrigley Field, or rent a rooftop!
Take a cruise on the Riverwalk on an Architectural Boat Tour.
Head to the Chicago Zoo and see the lions and ostrich! Its free! During COVID need reservations.
Walk the Lakefront
See a comedy show at Zanies and Second City (see links below)
 
Activities:
Play Pen- Must google!
Comedy Show at Second City or Zanies
Chicago Art Museum- Art Institute
Chicago Farmers Markets runs from summer to fall. There are a few markets, but my favorite is the one in Lincoln Park- Green City Market
 
Fun Times to Visit:
Fall to see the leaves changing.
Summer for fun on the lake and the beach experience
August for lollapalooza
Christmas time to experience the German Christmas markets, pack a coat: Christkindlmarket

cubs games.

riverwalk.                                        grant park.

chicago zoo.

aragon ballroom.

play pen.

christmas market.

architectural boat tour.

oriole.

lollapalooza.

robey hotel.