Guidebook for Chicago
Drinks & Nightlife
A personal favorite, this gastropub has a laidback atmosphere with a great beer garden and decent menu. Even better it’s only 5 mins walk away!
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Red Door Kitchen + Bar
2118 North Damen AvenueA personal favorite, this gastropub has a laidback atmosphere with a great beer garden and decent menu. Even better it’s only 5 mins walk away!
Sports bar with a nice outdoor patio area. Typical bar food on offer.
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Jack & Ginger's
2048 W Armitage AveSports bar with a nice outdoor patio area. Typical bar food on offer.
Our local, only minutes away. Great little corner bar, with a great atmosphere. Sometimes has a jazz band playing and if you’re lucky the tamale guy might show up. Cash only.
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The Charleston Bar Chicago
Our local, only minutes away. Great little corner bar, with a great atmosphere. Sometimes has a jazz band playing and if you’re lucky the tamale guy might show up. Cash only.
Part dive bar, part hipster hangout, Lottie's has something for everyone. The crowd is always lively, and there is usually good music/dancing. Plus, Chicago Fire and Chicago P.D. are both filmed here!
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Lottie's Pub
1925 W Cortland StPart dive bar, part hipster hangout, Lottie's has something for everyone. The crowd is always lively, and there is usually good music/dancing. Plus, Chicago Fire and Chicago P.D. are both filmed here!
Has a great outdoor patio area that is amazing in the summer and cozy in winter due to the fireplaces. Recommended for a few drinks and appetizers.
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Northside Bar & Grill
1635 N Damen AveHas a great outdoor patio area that is amazing in the summer and cozy in winter due to the fireplaces. Recommended for a few drinks and appetizers.
Trendy speakeasy that is very easy to miss (look for people queuing up alongside what appears to be just a wall). Has a dimly lit, cozy, intimate vibe. Drinks can be pricey though and expect to queue.
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The Violet Hour
1520 N Damen AveTrendy speakeasy that is very easy to miss (look for people queuing up alongside what appears to be just a wall). Has a dimly lit, cozy, intimate vibe. Drinks can be pricey though and expect to queue.
A must in the summer. Enjoy one of the many rooftop bars on offer.
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IO Godfrey Rooftop Lounge
127 W Huron StA must in the summer. Enjoy one of the many rooftop bars on offer.
The J. Parker
1816 N Clark StAnother rooftop,and another amazing view.
Enjoy Zed's steakhouse restaurant and then have some drinks in the rooftop bar.
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ZED451
739 N Clark StEnjoy Zed's steakhouse restaurant and then have some drinks in the rooftop bar.
Terrace 16
401 N Wabash AveGreat views. Pricey drinks.
Rooftop bar/club. Has a retractable roof so you can enjoy the outdoor feel, whatever the weather.
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ROOF on theWit
201 N State StRooftop bar/club. Has a retractable roof so you can enjoy the outdoor feel, whatever the weather.
Food Scene
Great little breakfast/brunch spot. Make sure to get there early so you don’t have to wait long and make sure to try the chicken sausage. Delicious!
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toast
2046 N Damen AveGreat little breakfast/brunch spot. Make sure to get there early so you don’t have to wait long and make sure to try the chicken sausage. Delicious!
Quiet neighborhood coffee shop that’s great for sandwiches, breakfast and brunch. Has a small outdoor seating area.
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Red June Cafe
2020 N Leavitt StQuiet neighborhood coffee shop that’s great for sandwiches, breakfast and brunch. Has a small outdoor seating area.
Great for hitting up on your way to the train. A must try is the Ipsento Latte (espresso, coconut milk, cayenne, honey, milk)! Has a small selection of breakfast items.
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Ipsento Coffee
2035 N Western AveGreat for hitting up on your way to the train. A must try is the Ipsento Latte (espresso, coconut milk, cayenne, honey, milk)! Has a small selection of breakfast items.
Birchwood Kitchen
2211 West North AvenueVery popular breakfast/brunch spot. Not open on Mondays.
Great service and good food. A favorite of ours is the Panang Curry. Even better, it’s BYOB.
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O'Cha Thai Cuisine
2062 N Damen AveGreat service and good food. A favorite of ours is the Panang Curry. Even better, it’s BYOB.
We love this place! BYOB, great food and atmosphere, what more can you want? Does not take reservations.
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Rangoli Classic Indian Dining
We love this place! BYOB, great food and atmosphere, what more can you want? Does not take reservations.
Another BYOB restaurant that comes highly recommended. Nice décor and atmosphere. Great for date night.
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Coast Sushi Bar
2045 North Damen AvenueAnother BYOB restaurant that comes highly recommended. Nice décor and atmosphere. Great for date night.
A 5 min taxi ride away that is well worth it. Delicious food centered on burgers. The truffle burger is to die for! Does not take reservations.
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Umami Burger Wicker Park
1480 N Milwaukee AveA 5 min taxi ride away that is well worth it. Delicious food centered on burgers. The truffle burger is to die for! Does not take reservations.
A staple take away option for us, but they also have $10 pitchers of sangria on Wednesdays. A favorite of ours is the Fidel Sandwich!
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Paladar Restaurant and Rum Bar
2252 N Western AveA staple take away option for us, but they also have $10 pitchers of sangria on Wednesdays. A favorite of ours is the Fidel Sandwich!
Very popular Costa Rican restaurant with an outdoor seating area. If you are looking for good food, fast service and a casual, relaxed but vibrant atmosphere, this is the one. BYOB and cash only.
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Irazu Costa Rican Restaurant & Catering
1865 N Milwaukee AveVery popular Costa Rican restaurant with an outdoor seating area. If you are looking for good food, fast service and a casual, relaxed but vibrant atmosphere, this is the one. BYOB and cash only.
A favorite in the Bucktown area, this tiny place has a small menu, but everything is done incredibly well and tastes delicious. Options include Korean tacos and Bibimbap. Does not take reservations.
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En Hakkore Bibimbap & Taco
1840 N Damen AveA favorite in the Bucktown area, this tiny place has a small menu, but everything is done incredibly well and tastes delicious. Options include Korean tacos and Bibimbap. Does not take reservations.
The priciest restaurant on this list, but with a great atmosphere and interesting food. This place also does brunch if you are looking for something a bit fancier than normal.
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The Bristol
2152 N Damen AveThe priciest restaurant on this list, but with a great atmosphere and interesting food. This place also does brunch if you are looking for something a bit fancier than normal.
Sweet pies, savory pies, candied bacon, breakfast biscuit, ham biscuit, sausage biscuit. Mouth watering goodness. Open all day.
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Bang Bang Pie & Biscuits
2051 N California AveSweet pies, savory pies, candied bacon, breakfast biscuit, ham biscuit, sausage biscuit. Mouth watering goodness. Open all day.
Shopping
Donuts to die for! We only came across this place recently but regularly make trips to satisfy our donut cravings. Try ‘The Dreamsicle’.
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Stan's Donuts & Coffee
1560 N Damen AveDonuts to die for! We only came across this place recently but regularly make trips to satisfy our donut cravings. Try ‘The Dreamsicle’.
Ice cream galore! A 5-minute walk to this retro ice cream store, and you will be in ice cream heaven. In the summer this place has a queue well into the night.
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Margie's Candies
1960 N Western AveIce cream galore! A 5-minute walk to this retro ice cream store, and you will be in ice cream heaven. In the summer this place has a queue well into the night.
Sightseeing
Check out the famous Bean or stroll through the Lurie Garden and take a break to dip your feet in the stream.
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Millennium Park
201 E Randolph StCheck out the famous Bean or stroll through the Lurie Garden and take a break to dip your feet in the stream.
Bring a picnic and enjoy the many free concerts and movie nights held here throughout the summer months.
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Jay Pritzker Pavilion
201 E Randolph StBring a picnic and enjoy the many free concerts and movie nights held here throughout the summer months.
In summer, try out the rock-climbing wall or mini golf. In winter, the mini golf is transformed into an ice skating ribbon. Bring your own skates to avoid queuing or rent a pair.
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Maggie Daley Park
337 E Randolph StIn summer, try out the rock-climbing wall or mini golf. In winter, the mini golf is transformed into an ice skating ribbon. Bring your own skates to avoid queuing or rent a pair.
Check out Buckingham Fountain or attend one of the many festivals held here throughout the summer. Highlights include Lollapalooza, Chicago Blues Fest and Taste of Chicago.
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I-Grant Park
337 E Randolph StCheck out Buckingham Fountain or attend one of the many festivals held here throughout the summer. Highlights include Lollapalooza, Chicago Blues Fest and Taste of Chicago.
Running for 18 miles along Lake Michigan, you can stop of at one of the many beaches and relax, or hire a Divvy bike and cycle along the lakefront. Also, try your hand at kayaking or paddle boarding.
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Lakefront Trail
Lakefront TrailRunning for 18 miles along Lake Michigan, you can stop of at one of the many beaches and relax, or hire a Divvy bike and cycle along the lakefront. Also, try your hand at kayaking or paddle boarding.
For the more adventurous, this is a great alternative to the traditional architecture tour.
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Urban Kayaks on the Chicago River
435 E. Chicago RiverwalkFor the more adventurous, this is a great alternative to the traditional architecture tour.
Fireworks - Wednesday and Saturday nights at 9.30pm during the summer. Head on down to Navy Pier or take a boat tour out on the lake to see the fireworks against the Chicago skyline.
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Navy Pier
600 E Grand AveFireworks - Wednesday and Saturday nights at 9.30pm during the summer. Head on down to Navy Pier or take a boat tour out on the lake to see the fireworks against the Chicago skyline.
Ride the elevator to the 96th floor and for the price of a drink (can be non-alcoholic), enjoy fantastic views of Chicago. This is often described as being cheaper and having a better view than Sears!
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The Signature Room at the 95th®
875 N Michigan AveRide the elevator to the 96th floor and for the price of a drink (can be non-alcoholic), enjoy fantastic views of Chicago. This is often described as being cheaper and having a better view than Sears!
FREE for everybody. Open all year, but can be crowded in summer. Other options include the Shedd Aquarium and Adler Planetarium (great skyline views out here too). These last two are not free.
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Lincoln Park Zoo
2001 N Clark StFREE for everybody. Open all year, but can be crowded in summer. Other options include the Shedd Aquarium and Adler Planetarium (great skyline views out here too). These last two are not free.
A favorite of ours! Other great museums include The Art Institute, The Field Museum and the Museum of Contemporary Art. Students can get reduced rates.
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Iziko Lomhlaba Wamaphupha Nokusebenza
5700 S Lake Shore DrA favorite of ours! Other great museums include The Art Institute, The Field Museum and the Museum of Contemporary Art. Students can get reduced rates.
Arts & Culture
Known for being the birthplace of many famous comedians. You may need to book tickets in advance, but you won't be disappointed. Other comedy venues include Zanies and the Comedy Bar.
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The Second City
230 W North AveKnown for being the birthplace of many famous comedians. You may need to book tickets in advance, but you won't be disappointed. Other comedy venues include Zanies and the Comedy Bar.
Wrigley Field
1060 W Addison StVisit Wrigley Field to cheer on the Cubs.
United Center
1901 W Madison StHome of the Bulls and the Blackhawks.
Isifunda seSoldier
1410 Special Olympics DrHome of the Chicago Bears.