Things To Do
Flight Club
Tyler and Moe spent a competitive anniversary here once and it has been a favorite spot ever since. Enjoy the great cocktails and unique dart games!
Chicago River Boat Architecture Tours
If you've never been, the Chicago Architecture Boat Tour is a must-see!
Millennium Park
Live like a tourist and visit "The Bean" and the beautiful Millennium and Grant Parks.
The Art Institute of Chicago
Truly one of Chicago's best museums!
Field Museum
Visit Chicago's Natural History Museum to see the world famous SUE the T.Rex and so many other gems. Tyler and Moe went on their 4th (and one of their best!) dates here on a beautiful day in February 2017.
Wrigley Field
Catch a Cubs game at iconic Wrigley Field! Cubbies play Friday and Sunday at 1:20 p.m.
Oak Street Beach
Take in the beauty of Lake Michigan. Sun yourself, walk the lakeshore or jump in the water if you dare!
The Berkshire Room
We love this cocktail bar! Tell them your spirit of choice, flavor profile and glass (highball, coupe, etc.) and they'll whip up a custom concoction. Be prepared for downtown Chicago prices. We think it's worth it!
West Loop / Fulton Market
Some of Chicago's best and trendiest restaurants are in the West Loop/Fulton Market area. Book your reservations in advance if you have something particular in mind. We're big followers of the restaurant review site The Infatuation so we suggest you take their advice! If you are looking at this and you did NOT plan in advance (Moe does this a lot...), we recommend Green Street Meats or Gus' World Famous Chicken. Sometimes you can get an early or late reservation at Duck Duck Goat too which is *chefs kiss* and great for groups.
Punch Bowl Social Chicago
Bowling, foosball, cocktails, and More! A great spot for a group to meet, drink, and play some games.
Emporium Fulton Market
Arcade Bar with lots of fun games (Frogger!) and great beer!
Eataly
Peruse this multi-story Italian marketplace with a glass of wine in hand. Get some imported goodies, grab an appetizer, or just take it all in.
Portillo's Hot Dogs
Get the ultimate Chicago experience at Portillo's. Whether it's a Chicago Dog, Italian Beef, or the Chopped Salad, you really can't go wrong!
LH Rooftop
Get a stunning view of the city from London House's Rooftop. Reservations recommended!
Cindy's Rooftop
Take in Millennium Park and a view of the Lake from Cindy's. Plus, great food! Reservations recommended!
Bavette's Bar & Boeuf
Best steakhouse in the city! If you're up for a fancy night out, this is Tyler and Moe's favorite restaurant. Reservations recommended! Pro tip: You can bring your own bottle of wine and not pay a corking fee if you agree to give out 1 glass from the bottle to a strangers table. It can be really fun!
Chicago Riverwalk
Goddess and the Baker, Riverfront
Great little cafe for a coffee, a baked good, breakfast or lunch.
Garrett Popcorn Shops
Get the Chicago Mix. You can thank us later.
Lou Malnati's Pizzeria
Get your fix of Chicago deep dish with The Malnati Chicago Classic pizza from "Lou's". The Malnati salad is also a must order!
Restoration Hardware / 3 Arts Club Cafe
Get an instagram worthy brunch at 3 Arts Club Cafe or grab a cocktail and walk the Restoration Hardware.
The Second City
Catch some sketch comedy at the famous Second City, where many well known comedians got their start.
Lincoln Park
Walk the park, check out the free zoo, nature walk, or conservatory! Cross the pedestrian path to the lake to check out North Ave Beach.
The J. Parker
Grab a bite or a drink at this rooftop hotel overlooking Lincoln Park.
The Signature Room at the 95th®
The best view of Chicago from the Hancock building's top floor!
Magnificent Mile
Get your shopping fix at Chicago's Mag Mile!
Doughnut Vault
These donuts are EPIC. Order at the window and enjoy!
Taste Of Randolph Street Fest
Known as "Chicago's most iconic street fest". Check out some great food and live music! Neighborhood street fests are a cornerstone of summer in the city! Entrance is "free" but a $10 donation is suggested.
Grant Park Music Fest
If you dig classical music, check out the Mendelssohn Reformation Symphony. Performed by the Grant Park Orchestra and Chorus at the Pritzker Auditorium in Grant Park Friday from 6:30-8:30 PM. It's free!