Illinois

THINGS TO DO 

Buckingham Fountain in Millennium Park.

If it’s nice out, take a walk down the lakefront trail.

River Architectural Tour:  Easy way to see the city! In the summer, you can do night tours on Wednesday/Saturday nights and see  fireworks over Navy Pier.

Second City Comedy: Many comedians from SNL got their start here. The shows are hilarious and definitely worth the price. Tickets are a little cheaper if you don’t go at peak times.

Signature Room at the John Hancock Building: Bar on the 95th floor with great views of the city, make sure you check out the views from the women’s bathroom.

Sky Deck in Sears Tower, check out their iconic glass floors!

The Bean a Chicago staple, formally dubbed “Cloud Gate,” this structure holds down the central plaza in Millennium Park. 

Violet Hour: A speakeasy in Wicker Park. Outer walls of the building are constantly changing color, so look for the single light bulb to find it!

Wrigley Field:  If you can’t check out a Cubs game, definitely still worth a visit to see the famous Wrigley Field sign. Stop by Sluggers for a drink after visiting the field and check out the batting cages on the second floor.

PLACES TO EAT

Au Cheval: Located in the West Loop neighborhood, you’ll find the best burger in the city. Doesn’t take reservations, but get the NoWait app to secure your place in line — grab drinks at any of the great restaurants/bars on Randolph Street afterwards.

Beatrix: Great brunch spot in the River North neighborhood.

Cafe Ba-Ba-Reeba!: Amazing tapas and a variety of alcoholic punches to go along with your meal. 

Girl and the Goat: Awesome tapas restaurant also in the West Loop neighborhood! Secure your reservation early though, this place can be fully-booked months in advance.

Happy Camper: Great traditional pizza spot in the Old Town neighborhood. It’s not deep-dish Chicago pizza, but still delicious pizza all the same.

Lou Melnati’s: Debatably the best deep-dish in the city. If that’s the style you’re looking for, Giordano’s and Gino’s are stellar alternates.  

Portillo’s: Make sure you grab a Chicago dog while you’re in town, and don’t put ketchup on it if you want to look like a native. Also worth ordering, check out their chocolate cake shake.

RM Champagne: The cutest bar/restaurant in the West Loop neighborhood. Expect great cocktails and great food.

Summer House: Stunning venue with great pizza. Perfect place to host a party. 

PLACES TO DRINK

River North: a little more high end/pricey. Typically, blend of established adults and young professionals.

Most venues have a bar feel on one floor and club on the others. Some fun ones to check: Hubbard Inn, Joy District, Celeste, Berkshire Room, Flamingo Rum Club, Three Dots and a Dash (Tiki bar). You can’t go wrong walking along Hubbard and seeing where the crowd is.  

Old Town: For a little bit of a younger crowd (ex frat stars), check out bars on Wells Street in Old Town.
Some of the more popular ones at night are: The Vig, Old Town Pour House, Benchmark, The Hangge Up (go late night, cash cover).

Wicker Park: Hip vibe, check out Wicker Park. Definitely the area with the most personality,
Some local spots: Slippery Slope, Deadbolt, Violet Hour (speakeasy), Revel Room (cocktails), Emporium, Tapster (quality beer), Black Bull (tapas and European soccer; hidden speakeasy through the walls and up the stairs), Map Room (global drinks and gin).

Lincoln Park: Almost exclusively young adults, Lincoln Park is located north of the touristy areas so you’ll mostly find locals.
A lot of fun bars, open until 4 a.m: Halligan’s, Hook and Ladder, Lion’s Head (young, club vibe upstairs), Danny’s (cash cover, but has different  dance rooms & a cool candlelight bar), Joe’s (turtle racing), Streeter’s/Beaumont (late night).

Favorite Rooftops

Londonhouse: Upscale with a great view of the river.
Cindy’s: Overlooks Millennium Park and the Bean.
J. Parker: Fantastic location to look out over the lake. 

PLACES TO STAY

The Loop: the business/financial district of Chicago — can be a quieter on weekends, but is still within walking distance of more touristy areas. 

Chicago Athletic Association: Classic hotel on Millenium Park, some say it’s haunted, but they will cater to your dog here. (Check out Cindy’s on the roof and the Game Room).

LondonHouse: Also located right on the river on Michigan Ave, walking distance to tons of tourist attractions. Rooms are decently priced and the hotel has a recently-open, amazing rooftop bar that offers a great view down the river.

River North

The Langham: Right on the riverside, expect it to be a little more pricey and bougie.

The Gwen: Boutique hotel also right in River North District, rooms are nice and also have a great rooftop bar.

Swissotel: Steps from the Chicago Riverwalk and luxury  shopping on the Magnificent Mile.

Gold Coast/Old Town

Lincoln Hotel: Bubbling with personality and right on the lake in the Gold Coast/Old Town neighborhood. Puts you in walking distance of all the bars and restaurants on Wells. Plus, they have a fantastic rooftop bar, the J. Parker.

Felix: Fairly priced, extremely tasteful and great location. The rooms are a tad on the smaller side

Wicker Park

The Robey: Located outside the touristy area of the Loop and River North, it’s got a beautiful rooftop pool. New hotel, and not a hipster crowd, despite it’s location in Wicker.