Best hidden gems in Chicago?

Not exactly a coffee shop and not exclusive to Chicago, but I think a great way to start the day is to go to DAVIDsTEA. From there you can head east to Lincoln Park Zoo or just beyond that to the beach, possibly Castaways if you are looking for a place to get a drink, but expect a crowd. 

It looks like the Cubs won't be in town until their Monday afternoon game but Wrigleyville is always a fun area to spend some time.  Other Chicago highlights usually include Skydeck Chicago for a view of the city and three other states on a clear day across the lake.  You can take an kayak archatectural tour if you're interested in that it is pretty interesting. 

My choice for comedy clubs is Second City, where tons of great talent got their start.  They are in Old Town at, 1616 N Wells St.  If you are looking for dinner before Twin Anchors is just a few blocks away and very well known for their ribs.  After the show if you want to stay in the area Benchmark or Old Town Social are good spots for drinks.

If you are into more of a craft beer scene I would suggest heading west to Wicker Park/Bucktown.  Fatpour Tap Works, The Boundary, and Bangers & Lace are all good places to start for wide varity.  Here are some good places for food in the area too, Black Bull for tapas, Frontier for some differnt/game like food, Big Star for tacos and whiskey, La Pasadita late night/quick tacos. 

If you are into shopping the Magnificent Mile has all your high end shopping.  While you are in the area you can go check out Millenium Park and be sure to take your picture at The Bean. 

Some more Chicago eats have to include pizza, and I would think you should try deep dish at Pizano's, Gino's East, Pizzeria UNO, or one of my two favorite's Lou Malnati's Pizzeria or Giordano's. Chicago Style hot dogs are another good idea if you are trying to check out what the city has some recognition for.  Portillo's Hot Dogs is one of the most well known not only for their dogs but also their beef sandwhich and chocolate cake.  The Wiener's Circle is a very entertaining late night food spot if you find yourself in some bars in the  Lincoln Park nieghborhood.  I love the food at Hub 51 and Carnivale.

Some other ideas for bars are Violet Hour or Three Dots and a Dash if you are into mixology.  Bub City or Old Crow Smokehouse for a country vibe. American Junkie, either of the Moes Cantina's, or John Barleycorn Rooftop's for a typical young bar scene. 

Local music at Double Door, Schubas, Lincoln Hall.  Some local and national cross over at places like The Vic Theatre, Aragon Entertainment Center, Metro.  Larger acts at places like House of Blues and a great place to see a show is FirstMerit Bank Pavilion at Northerly Island.  If you want to see some blue you can head to Buddy Guy's Legends or Kingston Mines.

I hope there is enough in here to give you a good taste of Chicago, it is a great city and I am sure I am leaving too much out.

Coffee shops: Bowtruss Coffee Roasters , La Colombe Torrefaction in Wicker Park, Dollop Coffee & Tea

Food: Ada Street is definitely a hidden gem. Your cab won't even know where they're taking you. But the space is awesome and the food is delicious. Big Star for tacos, micheladas and a great patio scene.  It's also just across the street from Violet Hour for cocktails.  Ruxbin Kitchen is also a great place and it's sister restaurant Mott Street is equally fun for elevated Asian street food. Check out their Sunday dinner if you can. Dusek's is good in Pilsen.  The Gage is centrally located (across the street from the Art Institute) but is delicious. Kinmont or Nico Osteria for seafood. Gilt Bar or Bavette's Bar and Boeuf for a late dinner. Green Street Smoked Meats for delicious casual BBQ in a cool setting. 

Drinks: People have already suggested Violet Hour. Watershed under Pops for Champagne is good in River North. The bartenders at Sable Kitchen & Bar also know what they're doing.  Punch House is below Duseks in pilsen and makes delicious punches. 

Brunch: The Bristol is good.  You absolutely cannot go wrong with The Publican. The same for Longman & Eagle or Lula Café if you venture out to Logan Square. 

Attractions: Definitely take an architectural boat cruise and make sure it take it though the Chicago Architecture Foundation River Cruise. Take the one that is just on the river if you really love architecture and want to learn about the buildings or take the one that is both river and lake if you don't care as much about architecture but want a beautiful view of the Chicago skyline. Rent a Divvy bike and bike along the lakefront. Make your way all the way down to Northerly Island for a gorgeous ride. 

Enjoy your time in Chicago. It's truly a great city and a hidden gem all on it's own. 

Here are a few of my favorite can't miss places in Chicago for a weekend trip.  For pizza, I would definitely recommend Pequod's Pizza...it gets my vote for the best deep dish pizza in the city!  

If you're into specialty cocktails, I would recommend The Barrelhouse Flat and speakeasy Violet Hour...their mixologists make some of the best cocktails in the city. 

For a comedy club, you can't go wrong with Second City...it's where a lot of the great comedians started and is always a good time.

If the weather is nice, stop by North Avenue Beach for great views of the city skyline.

Enjoy your trip!

So hard - so many good options to pick from! Here are a handful, hopefully this helps! Definitely agree with a lot of others here.

• Coffee: Bow Truss Coffee, Asado Coffee Co, Caffe Streets, Bourgeois Pig, Intelligentsia Coffee, New Wave Coffee, La Colombe Torrefaction. Kind of depends if you want the best coffee or coffee house atmosphere- some lean one way or the other 
• Restaurants: I could write a novel on this :) Some that come to mind that you won't find on popular lists (e.g. Eater): Ada Street, Tango Sur, Ruxbin Kitchen, Schwa (although impossible to get into!), Goosefoot (really amazing, highly recommend), Pequod's Pizza, Chicago Pizza & Oven Grinder Co (trust me). I really trust Eater so would check out their recos. too on where to eat now and best Chicago restaurants. They may not be "gems" but as a foodie trust me they always have the best recos.  
• Bars: in the summer you have to try a rooftop. My favorites are The Terrace at Trump Tower (expensive and fancier, but worth it) and The J. Parker at the Lincoln Hotel (trendier, best unobstructed view of the lake) Also love Violet Hour and The Barrelhouse Flat as others have suggested. Scofflaw is fun and different (a gin bar), The Aviary is definitely a cocktail experience (little pricey but worth it- connected with famed chef Grant Achatz), Longman & Eagle has great cocktails AND food... and don't forget- we have great breweries here so if you're into beer checkout the new Lagunitas Taproom, Revolution Brewing, Half Acre Beer Company, Piece Pizzeria and Brewery

I'll keep this short.

You need - NEED - to eat at Bite Café. It's "hidden" in the sense that it's out of the terrain of most Chicago travellers, nestled in the Ukrainian Village next to the best dirty music venue in the city - Empty Bottle.

I used to live two blocks from Bite and would go in every weekend for brunch. It's simply the most satisfying around. Sure, there are spots like Longman & Eagle that will blow the culinary roof off and destroy everything you knew about brunch, but Bite keeps the revolution simple and delicious. 

I rave about their brunch, but their dinner is fantastic too. Whatever you do, though - get a mashbrown there.

Second City is the most popular comedy club in Chicago, there are several stages and they generally all have well reviewed shows.  Weekend shows tend to sell out so you may want to book in advance.  Right next door is Adobo Grill where we usually eat when we go there.

If you want to try pizza, my two favorites are Lou Malnati's Pizzeria (multiple locations) or Giordano's (multiple locations), neither are hidden gems

Stop by the Chicago Cultural Center, the building is the old Chicago Public Library and the interior is fabulous, especially the staircase and Tiffany Dome on the Washington Street side.  Then walk a couple of blocks west to Macy's on State which used to be Marshall Field's and go to the Cllinique counter and look up for the beautiful Tiffany mosaic.  On the 7th floor is a gourmet food court including one of Rick Bayless' faster options, Frontera Fresco.  His other locations are also popular, Xoco is affordable and quick.

Not a hidden gem but if you like popcorn, stop by the Garrett Popcorn Shops on Randolph and grab a Chicago mix of caramel and cheese, just a couple of blocks from Macy's. 

On Sunday, if you like Mexican food, stop by the Maxwell Street Market which is no longer on Maxwell Street.  Great cheap Mexican food, look for the churro wagon.

If you like Chinese food, think about taking a Chicago Water Taxi down to Chinatown Chicago.  I especially like MingHin Cuisine for dim sum and Lao Sze Chuan for sit down Chinese and Joy Yee Plus for bubble tea.

If you are going with multiple people, look for a Groupon or Living Social deal to rent a pontoon boat and cruise the Chicago River. You get great views of the city and can relax for a few hours, eat and drink. Being on the water is so much fun! You can also kayak on the river too if you are feeling like getting some exercise. I would recommend finding a kayak place that is in the heart of the city though, because if you get too far north you won't get the greatest views of the city.

Boystown The Chicago Diner has amazing Sunday Brunch, and vegetarian Ruben's.  Nestled just outside of Wrigleyville, this place is really accessable.  

Zanies Comedy Club or Second City for comedy. Both on Wells in cool area.

Intelligentsia Coffee for coffee, The Fat Shallotfor food truck or Windy City Patty Wagon food truck.

Best brunch hidden gem - Grandma J's Local Kitchen in Humboldt Park. If you're there on a Monday, you should check out their burlesque + dinner: best hidden gem activity in Chicago!