Jennifer’s guidebook
Sightseeing
Great views of the skyline and Drake Hotel. Walk/Bike the lakeshore path along the beach. Entrance 1 1/2 blocks away.
7 locals recommend
Oak Street Beach
Great views of the skyline and Drake Hotel. Walk/Bike the lakeshore path along the beach. Entrance 1 1/2 blocks away.
The Drake hotel is down the street. There's shops, eateries, and restaurants open to the public so don't be shy and walk right in. It's a must see.
11 locals recommend
The Drake
140 E Walton PlThe Drake hotel is down the street. There's shops, eateries, and restaurants open to the public so don't be shy and walk right in. It's a must see.
The John Hancock not only has an Observation Deck, but they have a restaurant on the 95th floor AND a less known about lounge on the 96th floor if you want the views without the dinner price tag.
527 locals recommend
The Signature Room at the 95th®
875 N Michigan AveThe John Hancock not only has an Observation Deck, but they have a restaurant on the 95th floor AND a less known about lounge on the 96th floor if you want the views without the dinner price tag.
The Water Tower Mall is on Michigan Avenue. A great start to your walk down the Magnificent Mile. Across the street is the actual Old Water Tower; 1 of 7 buildings still standing from the Great Chicago Fire.
14 locals recommend
Water Tower Place
835 Michigan AvenueThe Water Tower Mall is on Michigan Avenue. A great start to your walk down the Magnificent Mile. Across the street is the actual Old Water Tower; 1 of 7 buildings still standing from the Great Chicago Fire.
Ferris Wheel Navy Pier Chicago
600 E Grand AveIf you want a Bird's Eye View and a cocktail, go to Cindy's across the street
473 locals recommend
Cloud Gate
201 E Randolph StIf you want a Bird's Eye View and a cocktail, go to Cindy's across the street
Buckingham Fountain
301 S Columbus DrTurns off end of Oct (Weather permitting)
Food scene
All within a couple blocks!
Sprinkles Chicago
50 E Walton StDid somebody say Cupcakes?
a nice small bar downstairs, a large lounge upstairs, and a separate dinning room for a great dinner!
35 locals recommend
Maple & Ash
8 W Maple Sta nice small bar downstairs, a large lounge upstairs, and a separate dinning room for a great dinner!
Lou Malnati's Pizzeria
1120 N State StDon't forget the butter crust
My favorite place for Brunch. This place is ALWAYS busy so be prepared to wait. This is one of the most popular restaurants in Chicago. Great for people watching and celebrity sightings.
85 locals recommend
Tavern On Rush
1031 N Rush StMy favorite place for Brunch. This place is ALWAYS busy so be prepared to wait. This is one of the most popular restaurants in Chicago. Great for people watching and celebrity sightings.
Delicious Italian food! They are pricey though! Otherwise, the lounge attached in the Nico hotel has one of my favorite lounges for drinks.
26 locals recommend
Nico Osteria
1015 N Rush StDelicious Italian food! They are pricey though! Otherwise, the lounge attached in the Nico hotel has one of my favorite lounges for drinks.
Gibsons Bar & Steakhouse
1028 N Rush StIt's Gibson's and it's around the corner!!!
Gorgeous restaurant/lounge w/ a light fare. It's also across the street!
25 locals recommend
Le Colonial Chicago
57 E Oak StGorgeous restaurant/lounge w/ a light fare. It's also across the street!
FIG & OLIVE
104 E Oak Stit's a few doors down and delicious
The Bar Scene
Divison street is 4 blocks away and known as the party street with bars open until 4am.
20 locals recommend
Hopsmith Chicago
15 W Division StDivison street is 4 blocks away and known as the party street with bars open until 4am.
Dublin Bar & Grill
1050 N State StA casual bar with a fun crowd that's open late
Neighborhoods
One neighborhood North from the Gold Coast, you'll find many bars and restaurants on wells street. I recommend The Vig for food, the Old Town Pour house for game day and Hotel Lincoln for day drinking with a rooftop view of the lake. Take the 36 bus direct.
49 locals recommend
Old Town
One neighborhood North from the Gold Coast, you'll find many bars and restaurants on wells street. I recommend The Vig for food, the Old Town Pour house for game day and Hotel Lincoln for day drinking with a rooftop view of the lake. Take the 36 bus direct.