. (singing) or the land of the free and the home of the brave.

playball! [music playing] water. the lifeblood of civilization. it's a source of food, transportation and commerce on which societies are built. but when you're 800 miles from the nearest ocean, you've got to make do with what you got. and for chicago, that's lake michigan, the largest body of water in the united states. so you can do quite a lot. and fittingly, one of the best ways to explore chicago is by boat as it flows right through the heart of the city.

chicago is unique in the fact that it's not just a lake town, but it's also a river town, as well. yeah, absolutely. and when you look at the river walk, there's recreation, there's kayaking. we truly want to make this a part of how we live here in chicago. i think the most impressive thing that you do is how you turn this water green. absolutely. we know how to celebrate st. patty's day here and what better way to do it than to turn the river green. i'll tell you what better way to do it. to celebrate the arrival of johnny bananas, you should have turned it yellow. (laughing) ok. problem is yellow water doesn't necessarily grab the right connotation. going through this waterway, i mean, it's like walking through an architecture art gallery. which ones are some of the iconic buildings? this one, right over here. this is marina city and you'll hear chicagoans refer to these as the "corncob" buildings. i can see why. this building is the willis tower, formerly, sears tower.

it held the title of the world's tallest building for over 20 years. what is it about chicago that made it so famous and so synonymous with architecture? of course, we have the chicago fire of 1871. we had to rebuild an entire city and that brought lots of great talent to the city. and from 1871, by 1885, we've got the world's first skyscraper here in chicago, and we have never stopped. i'm no architect, ok. but i don't know what is keeping that building from falling over. you know when you play jenga, and there's that jerk that pulls both blocks out so the whole tower's resting on one at the bottom? the engineer could do that. a lot of times when you think of major bustling, metropolitan cities they're usually on one of the coasts. we actually call chicago "the third coast." and i never, actually, thought i could love a city,

but then i came to chicago. and just walking around, i couldn't help but fall in love with everything around me. yeah. and falling in love is easy when you visit chicago's iconic navy pier, a wharf of wonder that juts out 3,300 feet onto lake michigan. today, it's hosting the annual race to mackinac island. a marathon sailing competition that attracts yacht teams from around the world. the water was calm, and it was time to sail. i just had to find the perfect boat. what is it about chicago that makes this such a haven for boaters? well access to the great lakes. this is the center of the united states for sailing and for boating. i see boats of all shapes and sizes. and you have sailors of all shapes and sizes, as well. no doubt. here at the burnham park yacht club we have a junior sailing program. each summer children can come and learn how to sail. they spend a week out on the water

and enjoy the wonderful sailing city of chicago. and after graduating sailing school with flying colors, i was more than ready to take on a little lake. my next instructor, race to mackinac veteran megan stole. a lot of people come here and they say i didn't know chicago was on an ocean. no, i didn't either. we can get conditions like an ocean, but, actually, a little worse. we can see waves that will crash over and come all the way to the back of the boat. we're going to be tacking and jiving. exactly, tacking and jiving. i just learned about tacking, but i've been talking jive since '95. tacking! what is the mackinac?

are we doing the mackinac right now? no. it is the oldest freshwater race in the world. it's 333 nautical miles from chicago up to mackinac island, which is on lake huron. so what does that translate to give or take in hours? this boat we can finish it in 42 hours. 40 hours straight? yeah. and you're saying, never again. never again. and then next year you're like. i'm doing it again. yeah. i'm sailing ma! i never would have thought that chicago would be considered a sailing town. the great lakes have fantastic sailing. it is quite a good backdrop. you know, we never tire of the skyline. who would win in a fight, a hurricane, or coach ditka? that's silly.

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walking around the windy city you can really feel a sense of pride in the air. chicagoans share a deep passion for their food, their music, and most of all, their sports teams. chicago has always been one of those cities where sports are a fabric of the society. i mean, the blackhawks-- three championships in six years. the bulls-- six championships in eight years. the '85 bears, and then you have the cubs in 2016, the white sox in 2005. this is a city of champions. it really is, man. yet despite all these championships, chicago is home to one of the most bitter rivalries in all of sports. the battle for baseball bragging rights between the north side cubs. everybody is either a cubs or a white sox fan. and there's no in between, right? and the south side white sox. are you a cub fan? or you're a white sox fan. but it's no gray, it's black or white. so to explore this duel on the diamond,

i visited the magical home turf of the white sox at guaranteed rate field to talk with baseball legend ozzie guillén. this is the banana man [speaking spanish].. as well as the iconic ivy walls of one of the league's most historic ballparks, wrigley field. to take some batting practice from former white sox and cubs outfielder, ryan sweeney. there goes. oh! it's kind of funny. my grandparents were huge cubs fans. so when i got drafted by the white sox, they were really happy for me. but they're like, i will cheer for you but i will not cheer for the white sox. how does that happen? throw a strike. that's stays is easy. just throw a strike. all right. strike. some people in chicago, man, they don't care about the season, they make sure we beat the cubs. when i'm managing the white sox, i say, ok we win the game, against the cubs, we have dinner in the restaurant. yeah, we beat the cubs! if we lose, mama had to cook in the house.

was there a side that resonated more with you, and the type of person that you are? like, describe the two different fan bases. well i just think, like, south side you think gritty, you know. you think, like, coming out there-- they are going to play hardball. well, south side is a bunch of blue collars people. blue collar. hard working. hard working guys, you know. back in wrigley field, it's different. you almost get that nostalgia, right. that history that you have behind the cubs, and you know, you're going to have the experience of wrigley field. wrigley field i always call the biggest bar in chicago. few people care about the game. they care about they winning just to celebrate. here, people sit down and watch the game, booing people, clap for people. it's a different expectation. listen, you've got the sox on the south side, you've got the cubs in the north side. even though we're talking about these two divergent fan bases, come the fall, it doesn't matter-- because the bears are it. the bears. i don't care if the white sox cubs win the next 10 years. nope, we are a bear.

and if you're going to talk bears, what better place than rizzo's sports bar and inn. the wrigleyville staple for over 75 years. - hey. - hey. hey, how are you doing? and gracing the taproom today is none other than bears hall of famer, dan hampton. and the greatest bear of all time, coach mike ditka. coach, you've been quoted as saying a lot of things. yesterday's history, tomorrow is a mystery. today is a gift which is why they call it the present. and i got to say today is a gift for me as a sports fan. so i appreciate you being here. i appreciate it. thank you very much. you know, coach, when i first got here to chicago, the legendary tales of you guys playing across the street here, in wrigley. we had a lot of fun. and it made me a cubs fan. i was a st. louis cardinals fan growing up because of stan musial. but i became a cubs fan, i'll always be a cubs fan. so now we know. so cubs. sox or cubs? - sox. - sox. cubs. i mean you got to be, you're right across the street. black hawks. black-- (chuckle).

coach, favorite memory as a player. the '63 championship. i mean, green bay, they were the best team in football. i mean, how the hell we beat them that year-- i don't know but we did. how about as a coach? super bowl '85. i thought you were going to say hanging out with me today. yeah, well, that's the second thing. i got to talk to you about that. i'll be honest with you the year we made it i was pretty sure we were going to make it. and we kicked ass and we took no names. we're like the rolling stones. we'd go into indianapolis, there'd be 5,000 people at the hotel. it was amazing. i used to say, we won the super bowl, we got rings, he got a halo. while chicago fans may have some disagreements on where they live, what teams they root for, at the end of the day-- we're all chicago. the greatest fans on earth. well, i think chicago is the greatest sports town in the world. pittsburgh is a great sports town. i'm from pittsburgh. but i'm a chicagoan, period. i mean cut and dry that's what i am. oh! don't make me charge the mound ryan.

stick to playing outfield man. what do you miss more, playing or being a manager? i've missing being playing. so you make a play in the shortstop to win the game, people are leaving with a smile on their face. oh, look at you see what ozzie did a base hit in the 9th. yeah, then they going to say, look at ozzie he was monitoring the 9th. one last question coach, who would win in a fight? a hurricane or coach ditka? that's silly. i have more hot air than any-- i love this guy.

there's so much to explore in this beautiful city. it seems like there's something to see around every turn. but to really know chicago, you have to learn about its history. and i think i just found the perfect guide. yo, what's up? it's your favorite neighborhood historian, dilla.

sherman "dilla" thomas is teaching the world about his beloved home one tiktok video at a time. on may 3, chicago got it's favorite skyscraper. today, i'm meeting dilla for a tour of chicago's south side. branded in the headlines for its high levels of crime, the south side is overlooked for its contributions to the birth of chicago. and yet, it's home to some of the city's most historical treasures. the man of the hour. - johnny. - you must be dilla. - that's me, baby. hey, good to meet you man. how are you? welcome to the south side. man, it's as beautiful as i'd imagined it. yeah, absolutely. you know, this is where the true chicago history is. you are one of these people that has taken tiktok, and instead of doing these viral dances, you're using it to educate. i want to highlight history. i want to highlight the city. i want to show that we're more than what the national media displays. so tell me a little bit about the significance of the statue behind us and this building here. formerly, the regal theater was in this spot, where every performer under the sun

was here. a lot of the greats-- lou armstrong, nat king cole. now, it's the harold washington culture center, chicago's first african-american mayor. and so i thought we can't start any kind of true south side tour without starting with the man himself harold washington. the chicago defender newspaper is very important-- not just to the city of chicago, but to the country. it's chiefly responsible for what we call the great migration. that's when african-americans in the millions moved from the south up north to various northern cities. the million african-americans that ended up in new york, arrived there because they were reading job applications that were published in the chicago defender, who's disseminated all around the country. so what are we looking at over here? sadly, this is the remains of pilgrim baptist church-- chicago's oldest black, baptist congregation. fire took place here in 2006, but the reason we're here is because it's the birthplace of gospel music.

i knew i was feeling a little bit of soul standing here. you know, right. so they always will tell you about the gang banger that comes out of chicago, but you won't hear how gospel music, right, praising the lord comes from chicago black south side. hallelujah. praise the lord. hallelujah. new york was a thing before america was america, right. that's why they're new york. same thing with any big city that comes from the 13 colonies. chicago is the first major city that comes after that. we're america's baby. and you know what you do with your baby? you spoil it. so that's why all the cool stuff comes from chicago. listen, i heard the barbecue here so good it'll make you want to slap your mama. this place is lem's. another example of how you don't need to go downtown to get fine cuisine. come right here on the south side of chicago-- get some of the world's best barbecue. what made you want to become such a history buff? well, primarily it comes from my father. my father was a chicago police officer for 30 years.

but he was a real big chicago history buff. so everywhere we went he kind of pointed out something. is this also a way for you to, kind of, almost like, carry on his legacy and keep his legacy alive? yeah, absolutely. and he left his impact on the city by being a chicago policeman, by touching lives. and so i want to do the same thing. we're in the neighborhood called the back of the yards. but i wanted to bring you here because a lot of times people think younger african-americans don't care about the police, or they don't care about the fire department. these murals pay homage to some of the fallen police officers who died in the line of duty. but we have amazing public art all throughout the city. it sprang up in celebration of juneteenth this year. so it's a new installation. one of my favorites is this piece right here, "a way to build a strong people is to teach their history. show them their roots." right. and so it's exactly what i'm trying to do on tiktok. show people the true roots of chicago and hopefully those roots sprout to something beautiful.

and it turns out we weren't the only ones enjoying these south side murals, so was chicago mayor lori lightfoot. again, if there's anything i can do for my city i'm not hard to reach. i am going to keep doing only positive chicago stuff. right. i really appreciate it. truly an incredible ambassador to this city here. what you're doing out here, on social media, community outreach, i can tell man that you are an absolute pillar of this community. and i just want to say thank you for showing me around and showing me just how colorful chicago can be. i'm morgan, and there's more to me than hiv. more love, more adventure, more community. but with my hiv treatment, there's not more medicines in my pill.

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use effective birth control while on dovato. do not breastfeed while taking dovato. most common side effects are headache, nausea, diarrhea, trouble sleeping, tiredness, and anxiety. so much goes into who i am. hiv medicine is one part of it. ask your doctor about dovato-i did. ♪♪ every day in business brings something new. so get the flexibility of the new mobile service designed for your small business. introducing comcast business mobile. you get the most reliable network with nationwide 5g included. and you can get unlimited data for just $30 per line per month when you get four lines or mix and match data options. available now for comcast business internet customers with no line-activation fees or term contract required. see if you can save by switching today. comcast business. powering possibilities.

when i come to town i come to party. and the club scene here in chicago, is just what the doctor ordered. but on the north side of town is a different kind of club. there's no dj here but the music plays all night long. the music never stops. it's got two stages. you can come here in the summer-- the sun's up and when you leave-- the suns up. this ain't for chickens. - no, this ain't for chickens. no. founded in 1968, by doc pellegrino, kingston mines was one of the first interracial blues clubs in the city.

a proud legacy that's still being carried on by doc's children and grandchildren today. he wanted people to come together from all walks of life. ok. and have a good time. when you come here and there's only two people, and it's a table of eight or 10, other people just come up and sit down with you. it just brings a lot of people together. they listen to good music. stuff that they normally wouldn't listen to. the whole idea was to make people feel at home. that this is their home away from home. what is it about the blues that has the ability to, like, almost speak a common language to so many different walks of life? i love the honesty of it, the realness of it, the passion of it. you know, it's great music to let things go. it's great music to celebrate. as a one single common bond for all these people-- the music is healing. this is joanna connor! and tonight, the healing hands belong to none other than joanna connor.

the brooklyn native, turned chicago shredder, never fails to pack the house. people love her and she plays guitar like no other woman i've seen. when i play guitar, i get kind of aggressive. i don't know, i just go into that zone "i want to kick some butt," you know. did you like that? do you ever get nervous when you come up here? i get nervous every night. every time? when you can lose that, it means you lost your passion. i'm a bit nervous. is this normal? got to get that wine going. all right. hey. hey, man. to drinking red and playing the blues. are you feeling good, chicago? [cheering] all right. are you feeling good, johnny bananas? he's still worried. he's ready. so we're going to play a little blues for you. how's that sound? [blues music]

(singing) [inaudible] turn your light down low. blues in chicago is synonymous. blues is a gift to the world. and it really launched from here. i used to go see all the chicago blues bands when they'd come through i lived. and i was like, i'm moving to chicago. (singing) so sweet and nice. hey. hey. blues music is about where you been, where you're going to, and where you're at right now. you want to feel it, but not necessarily only in your eardrums. you want to feel it right here. exactly. and that's really what music is all about. [blues music]

yeah! the wine worked didn't it? we got to take this show on the road, joanna.

i'm sara gore, and this is "open house." this week, we are all about manhattan luxury, design, and style. uptown and downtown,n the bowery and off of gramercy, sophisticated homes with a flair for the dramatic