Cocktails
Interesting and amazing cocktails. Building owned by a woman named Mary in her late 80's. That's where the name came from. The inside of the bar looks like it might be an old ship.
40 locals recommend
Queen Mary
2125 W Division StInteresting and amazing cocktails. Building owned by a woman named Mary in her late 80's. That's where the name came from. The inside of the bar looks like it might be an old ship.
Estereo
2450 N Milwaukee AveAll day bar. Tropical cocktails and music. No food.
Speak easy downstairs from Dusek’s restaurant in Pilsen. Really good cocktails.
78 locals recommend
Punch House
1227 W 18th StSpeak easy downstairs from Dusek’s restaurant in Pilsen. Really good cocktails.
Scofflaw
3201 W Armitage AveGreat cocktails. Get the burger. Comparable to the burger at Au Cheval.
Bordel
1721 W Division StCabaret shows and cocktails. What more could you want? Need a reservation.
Cozy, stylish bar at the Chicago Athletic Association serving cocktails made with rare ingredients.
Only seats 10 and requires a reservation and deposit.
7 locals recommend
The Milk Room
12 South Michigan Avenue
Cozy, stylish bar at the Chicago Athletic Association serving cocktails made with rare ingredients.
Only seats 10 and requires a reservation and deposit.
The Hoxton, Chicago
200 N Green StThe bar in the lobby is pretty good.
Wine Bar
Best wine bar in Chicago. Approachable wine list and food menu. Casual and friendly with a nice outdoor patio. Great service and easy to get to via car/taxi/Uber or bus.
173 locals recommend
Rootstock Wine & Beer Bar
954 North California AvenueBest wine bar in Chicago. Approachable wine list and food menu. Casual and friendly with a nice outdoor patio. Great service and easy to get to via car/taxi/Uber or bus.
Great wine selection. Easily accessible by blue line train. Parking can be a challenge, so public transportation or taxi/uber is best.
73 locals recommend
Websters Wine Bar Chicago
2601 N Milwaukee AveGreat wine selection. Easily accessible by blue line train. Parking can be a challenge, so public transportation or taxi/uber is best.
Speak easy type wine bar in the basement of a bed and breakfast. Eat by candlelight. Great wine and cocktail list. Amazing food and service. You'll need a reservation.
8 locals recommend
The Press Room
1134 W Washington BlvdSpeak easy type wine bar in the basement of a bed and breakfast. Eat by candlelight. Great wine and cocktail list. Amazing food and service. You'll need a reservation.
The only winery in the city. Great event space. Concerts every weekend. You need tickets to attend the concerts so check ahead for who is playing. Huge outdoor space.
70 locals recommend
City Winery
1200 W Randolph StThe only winery in the city. Great event space. Concerts every weekend. You need tickets to attend the concerts so check ahead for who is playing. Huge outdoor space.
Neighborhoods
Bustling with young professionals, hip shops, restaurants, bars, coffee shops, bakeries, etc. You could spend a whole day in this neighborhood eating, drinking and shopping. Accessible via the bus, train, taxi or uber. Parking can be a challenge, so I would not recommend driving yourself.
89 locals recommend
West Loop
Bustling with young professionals, hip shops, restaurants, bars, coffee shops, bakeries, etc. You could spend a whole day in this neighborhood eating, drinking and shopping. Accessible via the bus, train, taxi or uber. Parking can be a challenge, so I would not recommend driving yourself.
Bustling with young professionals, hip shops, restaurants, bars, coffee shops, bakeries, etc. You could spend a whole day in this neighborhood eating, drinking and shopping. Accessible via the bus, blue line train, taxi or uber. Parking can be a challenge, so I would not recommend driving yourself. If you take the train, exit at North Ave/Milwaukee/Damen.
55 locals recommend
Bucktown
Bustling with young professionals, hip shops, restaurants, bars, coffee shops, bakeries, etc. You could spend a whole day in this neighborhood eating, drinking and shopping. Accessible via the bus, blue line train, taxi or uber. Parking can be a challenge, so I would not recommend driving yourself. If you take the train, exit at North Ave/Milwaukee/Damen.
Written about as the most popular neighborhood in the United States for a couple of years. Artists and hipsters occupied Logan Square making way for art galleries, restaurants, bars, shops, coffee shops and beautiful city parks.
174 locals recommend
Logan Square
Written about as the most popular neighborhood in the United States for a couple of years. Artists and hipsters occupied Logan Square making way for art galleries, restaurants, bars, shops, coffee shops and beautiful city parks.
Historically a Mexican neighborhood. A melting pot of many different cultures and people. Young artists have started to occupy apartments and studios here. Still predominantly occupied by Mexican families. You will find some of the best Mexican food you've ever had.
103 locals recommend
Pilsen
Historically a Mexican neighborhood. A melting pot of many different cultures and people. Young artists have started to occupy apartments and studios here. Still predominantly occupied by Mexican families. You will find some of the best Mexican food you've ever had.
Sightseeing
Similar to the Highline in NYC. It was an old elevated train track that was decommissioned and turned into a beautifully landscaped bike and running path. There are benches to sit and relax throughout the path.
241 locals recommend
The 606
1805 North Ridgeway AvenueSimilar to the Highline in NYC. It was an old elevated train track that was decommissioned and turned into a beautifully landscaped bike and running path. There are benches to sit and relax throughout the path.
Check out the website for all that Millenium Park has to offer. https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park.html
1243 locals recommend
Millennium Park
201 E Randolph StCheck out the website for all that Millenium Park has to offer. https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park.html
Willis Tower
233 S Wacker DrGet tickets ahead of time. They usually sell out weeks in advance.
360 degree views of the city. On clear days you can see all the way to Iowa. The best view is in the ladies room! If you don't want to have a full dinner, check out their lounge/bar on the 96th floor. You might need to make reservations. Check ahead of time.
523 locals recommend
The Signature Room at the 95th®
875 N Michigan Ave360 degree views of the city. On clear days you can see all the way to Iowa. The best view is in the ladies room! If you don't want to have a full dinner, check out their lounge/bar on the 96th floor. You might need to make reservations. Check ahead of time.
Check exhibits ahead of time. The modern wing is usually really interesting. Parking is expensive.
1159 locals recommend
The Art Institute of Chicago
111 S Michigan AveCheck exhibits ahead of time. The modern wing is usually really interesting. Parking is expensive.
Museum of Science and Industry
5700 S Lake Shore DrOne of my faves.
The Field Museum
1400 S Lake Shore DrCheck the website for exhibits
Shopping
Chicago souvenirs that locals would buy. The owner designs and sews lots of the clothing. Really cool boutique shop that you wouldn't find tourists visiting.
65 locals recommend
Wolfbait & B-girls
3131 W Logan BlvdChicago souvenirs that locals would buy. The owner designs and sews lots of the clothing. Really cool boutique shop that you wouldn't find tourists visiting.
Food scene
Great place for tacos and cocktails. Amazing outdoor space. Fun and hip atmosphere. Right next to the North Ave/Damen/Milwaukee blue line train.
1174 locals recommend
Big Star
1531 N Damen AveGreat place for tacos and cocktails. Amazing outdoor space. Fun and hip atmosphere. Right next to the North Ave/Damen/Milwaukee blue line train.
Nashville style chicken, hush puppies, fish and chips. Get a slushie! They're delicious. If you can get a table outside, it's worth it. Casual and fun. There is usually a wait to get in. Anywhere from 30 minutes to 2 hours.
658 locals recommend
Parson's Chicken & Fish
2952 W Armitage AveNashville style chicken, hush puppies, fish and chips. Get a slushie! They're delicious. If you can get a table outside, it's worth it. Casual and fun. There is usually a wait to get in. Anywhere from 30 minutes to 2 hours.
One of the largest whiskey selections in the U.S. Upscale food, cocktails, wine and beer. Great service. Across the street from the Logan Square blue line train station.
830 locals recommend
Longman & Eagle
2657 N Kedzie AveOne of the largest whiskey selections in the U.S. Upscale food, cocktails, wine and beer. Great service. Across the street from the Logan Square blue line train station.
Pub Royale
2049 W Division StIndian food in an English pub setting with a large selection of beer
Beautifully designed and decorated with a tropical Mediterranean vibe. Great food and cocktails. Need a reservation.
78 locals recommend
Beatnik
1604 W Chicago AveBeautifully designed and decorated with a tropical Mediterranean vibe. Great food and cocktails. Need a reservation.
Great selection of food and cocktails. Nice outdoor space. You will need a reservation. Parking is challenging. Take a taxi/uber or public transportation.
Perilla | korean american fare
401 North Milwaukee AvenueGreat selection of food and cocktails. Nice outdoor space. You will need a reservation. Parking is challenging. Take a taxi/uber or public transportation.
One of the best burgers in Chicago. Get there early and get your name on the list. They don’t take reservations so you could wait for an hour or more for a table.
620 locals recommend
Au Cheval
800 W Randolph StOne of the best burgers in Chicago. Get there early and get your name on the list. They don’t take reservations so you could wait for an hour or more for a table.
Osteria Langhe
2824 W Armitage AveCasual place. Italian cuisine. Great service. Cute space.
One of the best steak houses I've ever been to. It's small so there is limited seating. You need a reservation.
57 locals recommend
BoeufHaus
1012 N Western AveOne of the best steak houses I've ever been to. It's small so there is limited seating. You need a reservation.
Not your traditional steak house. Great selection of steak and seafood.
79 locals recommend
Bavette's Bar & Boeuf
218 W Kinzie StNot your traditional steak house. Great selection of steak and seafood.
Next door to Thalia Hall. Cocktail bar in the basement (speak easy) called the Punch Room.
155 locals recommend
Dusek's Board & Beer
1227 W 18th StNext door to Thalia Hall. Cocktail bar in the basement (speak easy) called the Punch Room.
One of the best Ramen restaurants in Chicago. They also have sushi. Great selection of Japanese spirits as well. It's usually packed. I would advise a reservation.
134 locals recommend
Ramen Wasabi
2101 N Milwaukee AveOne of the best Ramen restaurants in Chicago. They also have sushi. Great selection of Japanese spirits as well. It's usually packed. I would advise a reservation.
KAI ZAN
2557 W Chicago AveSmall space. Limited seating. Need reservations. Best sushi in the city
JJ Thai Street Food
1715 W Chicago AveNot your typical Thai food. Unique dishes.
Lao Peng You
2020 W Chicago AveIt’s small, casual and BYOB. Delicious noodle dishes.
Contemporary American cuisine with international flair. Great service. The tasting menu is usually really good. Need a reservation.
28 locals recommend
S.K.Y.
1239 W 18th StContemporary American cuisine with international flair. Great service. The tasting menu is usually really good. Need a reservation.
If you’re into deep dish pizza, look no further. Best deep dish in Chicago.
512 locals recommend
Lou Malnati's Pizzeria
1120 N State StIf you’re into deep dish pizza, look no further. Best deep dish in Chicago.
Girl & The Goat
809 W Randolph StStephanie Izard’s restaurant. Need a reservation.
If you’re a carnivore, you’ll love this place. Great for brunch too.
60 locals recommend
Publican Quality Meats
825 W Fulton MarketIf you’re a carnivore, you’ll love this place. Great for brunch too.
Great happy hour. Unique cocktails. One of our favorite places.
11 locals recommend
Heritage Restaurant & Caviar Bar
2700 W Chicago AveGreat happy hour. Unique cocktails. One of our favorite places.
Lesbian owned. Wine list includes women and minority vintners. GREAT food!
19 locals recommend
Split-Rail
2500 W Chicago AveLesbian owned. Wine list includes women and minority vintners. GREAT food!
Dive bar
Upscale bar food and great selection of beer. Nice outdoor seating.
41 locals recommend
Tuman's Tap and Grill
2159 W Chicago AveUpscale bar food and great selection of beer. Nice outdoor seating.
Upscale cocktails. Bar food. Hipster paradise. Great outdoor space in the back.
45 locals recommend
Best Intentions
3281 W Armitage AveUpscale cocktails. Bar food. Hipster paradise. Great outdoor space in the back.
Lone Wolf
806 W Randolph StCasual place. Great spot to wait for your table at Au Cheval.