EATS
Pequod’s Pizza
Un-traditional deep dish pizza – we think it’s the best.
Transportation: Easiest to take a cab.
2207 N Clybourn Ave (between Webster Ave & Greenview Ave)
Ian’s Pizza by the Slice
Great thin crust, unique ingredients (like Mac ‘n Cheese)
Transportation: Red Line (Addison Stop) or Clark Bus
3463 N Clark St. (cross-street Cornelia)
Billy Goat
Cheeseburgers, and only cheeseburgers, at the famous tavern. Make sure to read about how the Billy Goat cursed the Cubs before you go!
Transportation: Red Line (Grand Stop)
430 N Michigan Ave. (Lower level)
Rock Bottom
Great pub food and beer brewed onsite – this is also where Brandon and Helen met (just sayin’).
Transportation: Red Line (Grand Stop)
1 West Grand Ave. (Cross-Street: State)
Haymarket
Another great brewery (if you can’t tell we like beer, and admire those who make it really well)
Transportation: Cab it
737 W Randolph St. (Cross-Street: Halsted)
Sweetwater Tavern & Grille
Great place to eat after shopping on the Mag Mile, or while checking out some of the sites by the Loop.
Transportation: By the Loop and therefore like every train line (Lake Stop) or the buses on Michigan
225 North Michigan Avenue (Between South Water and Lake)
Portillo’s
Amazing Italian beef sandwich – don’t forget the hot peppers!
Transportation: Red Line (Grand Stop)
100 W. Ontario (Between LaSalle & Clark)
Hot Doug’s
Delish, fancy hot dogs (be ready to wait in line)
Transportation: Cab it
3324 North California Ave
Xoco
Do you like Rick Bayless? We sure do. Try this quick service cafe instead of waiting a couple of months to get a reservation at Frontera.
Transportation: You guessed it – Red Line (Grand Stop)
449 North Clark Street (Cross-Street: E. Illinois)
DRINKS
Sig Room at Hancock Building
The best view in Chicago, bar none. The bar area serves top of the line drinks that are expensive, but worth the view alone.
Transportation: Red Line to Chicago Ave. (then a 3-4 block walk east to that really tall building)
875 North Michigan Avenue
Violet Hour
One of the coolest and swankiest bars out there. It’s a throwback to the speakeasy and doesn’t have a sign or even a door. Seriously. The door is hidden.
Transportation: Blue Line to Damen
1520 North Damen
Timothy O’Tooles
A fun little Irish sports bar downtown. Nothing too special, but a solid bar.
Transportation: Red Line to Grand
622 North Fairbanks Court
Watershed Bar (below Pops for Champagne)
Hidden below one of the nations premiere champagne bars is a cool little bar that specializes in great mixed drinks. Moscow Mules served in a copper cup anyone?
Transportation: Red Line to Grand
601 North State Street
SIGHTS
Field Museum & Shedd Aquarium
Check out Sue the T-Rex and her friends at the Field Museum. Then keep walking and hit Shedd Aquarium. Great place to take your kids if they are into history, sea animals, and cool dinosaurs.Transportation: Red or Orange Line to Roosevelt (then a 4+ block walk)
1400 South Lake Shore Drive
Millennium Park, Art Institute & Grant Park
All of these great spots are within a 1-mile stretch of Michigan Ave. See the Bean, Buckingham Fountain, the faces in Crown Fountain and more.
Transportation: These are all down by the Loop. Check out the link to Google maps above.
201 E. Randolph Street
Lincoln Park Zoo
There is no admission fee for this great public zoo right in the middle of Chicago.
Transportation: Cab or #22 Clark Bus to Wisconsin Stop
2200 N. Cannon Drive
Navy Pier
This is kind of tourist central – but if you’ve never been to Chicago it’s a great place to see. You can get a great view of the city from the giant Ferris Wheel.
Transportation: Check out the buses that hit the pier at http://www.navypier.com/visit_us/pub_trans.html
600 E. Grand Ave
Architectural Tour
See the beautiful buildings of Chicago on a boat – there are a ton of companies that offer tours – you’ll likely run into the sales people walking around the city. The Chicago Historical Society offers a good one – which is linked here.
465 North McClurg Court
Bike Rentals & Segway Tours
One of our favorite things to do is bike along the lake on the bike path. Check out rentals and tours at http://www.bikechicago.com/
Lake Front / Beach
From Edgewater to Ohio Street – there are beaches running along most of Chicago. June weather is a great time to go swim, relax, or play some beach volleyball.
1000 North Lake Shore Drive
Improv Olympic Theater
Check out some of the best improv teams here – we can guarantee you great laughs and cheap drinks.
Transportation: Red Line Addison Stop
3541 North Clark Street
Howl at the Moon
Check out the dueling piano bar here for a unique and fun experience.
Transportation: Red Line Grand Stop
26 West Hubbard Street (Between State and Dearborn)
Kingston Mines
This is the place to listen to blues – a Chicago landmark.
Transportation: Brown or Red Line to Fullerton Stop
2548 North Halsted Street
Schuba’s
Great, small venue to see some music, eat good food and drink yummy drinks.
Transportation: Brown Line Southport Stop or Red Line Belmont (then a short walk)
3159 North Southport Avenue (Cross-street Belmont)