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NameActivity TypeLocationDescriptionCostLink
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Lake Shore TrailPark
All the neighborhoods ~
Walk along the lake!Free
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Ranallis of AndersonvilleFoodAndersonvilleFavorite pizza in the city. Order thin crust, peperoni + roasted peppers + extra sauce + extra crispy.$$
http://www.ranallisofandersonville.com/
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Little Bad WolfFoodAndersonvilleFavorite burger in the city. This place can get busy in the evening but if you find your way up north, you gotta try the burger and mac (they also have lumpia!)$$
https://www.littlebadwolfchicago.com/
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Clark St AndersonvilleShoppingAndersonvilleMain strip has so many cute shops and knick knack stores. Literally a perfect day when I lived there was just walking the strip and hopping in and out of shops.$-$$
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Margies CandiesDessertBucktown
Really cute 1950s diner style place! It was in the bear. Back in the day, Victor's grandparents used to go there and be cute.
$
https://www.margiescandies.com/
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Chef's SpecialFoodBucktown3 min. from my house. Award winning Asian fusion served family style.$$
https://chefsspecialbar.com/menu/
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Leavitt Street TavernFood/ DrinksBucktownWe waited an ungodly amount of time for food on a Friday so I rec. a reservation, but they have a really good smash burger and aioli for fries.10 min. walk from my apartment.$-$$
https://www.theleavittstreet.com/
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Maplewood BreweryDrinksBucktownChill industrial vibes$ - $$
https://maplewoodbrew.com/verify?redirect=https://maplewoodbrew.com/
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Italian IceDessertBucktown/ Little Italy
Very Chicago dessert - cool and refreshing in the summer. Two location recs, one is Ava's in Bucktown (12 min from my apt.) and Mario's Italian Lemonade on Taylor Street.
$
https://avasitalianice.com/
http://marioslemonade.com/
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MCCB (Modern Chinese Cookbook)FoodChinatownHonorable mention - if you're downtown, have fun, take the water taxi to Chinatown! It's not as big as SF's but it's cute to walk around. Award winning. I had a steak and bell pepper dish here and those were some of the best bell peppers I've ever had.$$
https://www.mccbchicago.com/
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Ponce RestaurantFoodHermosaPuerto Rican Restaurant - tried their food at Puerto Rican fest and it was good!$$
https://www.poncerestaurant.com/menu
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Eris Brewery and CideryFood/ DrinksIrving ParkBomb food (Victor's fav is the mac and cheese and briskey) + drinks.$$
https://www.erischicago.com/
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Replay BarcadeDrinksLincoln ParkArcade Bar. It will be Pirates of the Caribbean themed when you're here.$$
https://www.replaylincolnpark.com/
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Linzoln Park ZooMuseumLincoln ParkFree zoo that's really nice!Free
https://www.lpzoo.org/
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Lincoln Park ConservatoryMuseumLincoln ParkClose to the zoo, it's an indoor greenhouse with a butterfly room I believeFree
https://www.lincolnparkconservancy.org/projects/conservatory-garden/
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Pasta BowlFood
Lincoln Park/ Wicker Park
Yummy pasta, huge portions.$$
https://www.pastabowl.com/
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The Lincoln LodgeComedyLogan SquareLongest running stand up comedy nonprofit in the US. Affordable tickets/ drinks. Like always, some comedians can be hit or miss lol but we love the vibes.$-$$
https://www.thelincolnlodge.com/
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Revolution BrewDrinksIrving ParkOne of the more popular breweries.$ - $$
https://revbrew.com/visit/brewery
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Jibaritos y MasFoodLogan SquareThe jibarito is a sandwich that uses fried plantains instead of buns. It's a Puerto Rican dish founded in Chicago!$
https://www.jibaritoschicago.com/
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Saba Italian Bar and KitchenFoodLogan SquareItalian food, we went there during restaurant week. Nice portions. Close to a bar I love called the Old Plank.$$
https://sabaitalian.com/
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Starbucks Reserve Roastery ChicagoDrinksLoop (Downtown)Okay - hear me out. I also don't like coffee, but this is the largest Starbucks and it's cool to walk through! It's four floors with a bar at the top floor.$ - $$
https://www.choosechicago.com/blog/worlds-largest-starbucks-chicago/
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Cindy's RooftopFoodLoop (Downtown)I've finally went earlier this year! Nice apps/ drinks and is truly one of the most beautiful views of Millenium Park. Reservations highly recommended.$$-$$$
https://www.cindysrooftop.com/
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Wildberry CafeFoodLoop (Downtown)Brunch. I've been to the one in the Suburbs. It's good. Standard brunch.$$
https://wildberrycafe.com/locations/chicago-prudential-plaza
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London HouseFood/ DrinksLoop (Downtown)I've never been but it's a hotel with a sick rooftop bar right off the Riverwalk with a beautiful view of the city.$$- $$$
https://londonhousechicago.com/rooftop/
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Chicago City PassMake your own adventureLoop (Downtown)If you want to do several things while you're here, check out the Chicago City Pass. Essentially it gets you admission to up to 5 attractions (including the Sky Deck where you can stand on the glass floor).$$$
https://www.citypass.com/chicago-comparison
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Art MuseumMuseumLoop (Downtown)Beautiful art museum with cool art! Ranges from ancient cultural, photography, and modern art. Let me know if this is something you're interested in and I can get a guest pass through my work.Free - $$
https://www.artic.edu/
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Millenium ParkParkLoop (Downtown)See the bean! Dip your toes in a public water sculpture. See different outdoor art installations and the beautiful Buckingham fountain. Right by it is South President's Court if you're curious to see where Victor proposed lol.Free
https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park.html
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Art on the MartParkLoop (Downtown)9 PM. Cool projected art show on the Merchandise Mart building. There are benches along the riverwalk where you can sit and watch. There's also an audio component playing on speakers.Free
https://artonthemart.com/
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RiverwalkPark/ Drinks/ FoodLoop (Downtown)1.25 miles of sidewalk along the River with bars and restaurants along the way! Perfect for eating or enjoying a nice cool drink outside by the water. Great spot to people watch. Tacorio is at the beginning of the Riverwalk closest to the lake.Free
https://www.chicago.gov/city/en/sites/chicagoriverwalk/home.html
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Architecture Boat TourRiverLoop (Downtown)Hands down one of the things I recommend everyone who visits should do. It's a great way to learn about the city's history, appreciate the skyline, and just see the city from a new perspective out on the water. Listed are two options$$
https://www.groupon.com/deals/gl-chicago-architecture-boat-tours-2024
https://www.architecture.org/tours/detail/chicago-architecture-center-river-cruise-aboard-chicago-s-first-lady/#tickets
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Magnificent MileShoppingLoop (Downtown)This street has a lot of stores. $ - $$$
https://www.themagnificentmile.com/shopping/
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Second CityComedyOld TownBig historical comedy place. I've never been but big names like Tina Fey and Amy Poehler got their start there.$$
https://www.secondcity.com/
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Frontera Mexican GrillFood
River North (Downtown)
Restaurant owned by Rick Bayless. Victor went to during restaurant week - he said it was good.$$
https://www.fronteragrill.com/
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Piccolo SognoFood/ Drinks
River West (Downtown)
Fancy Italian restaurant Victor went to for restaurant week. He said they had good wine.$$-$$$
https://www.piccolosognorestaurant.com/
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Lou Malnatis/ Giordanos/ PequodsFoodVariousFind yourself some deep dish-
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BokaFoodWest LoopNever been but people say it's good - Michillen star restaurant. Rec. reservation.$$$
https://www.bokachicago.com/
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National Museum of Mexican American Art
PilsenAmazing free museum - largest collection of Mexican American art.Free
https://nationalmuseumofmexicanart.org/
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Rubi'sFoodPilsenAward winning large portion tacos$-$$
https://rubischicago.square.site/
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Luna Cafe RestaurantFoodPilsenBomb Chillaquiles$$
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La CeliaFoodAvondaleCasual Cuban food with fun wall art/ paintings$-$$
https://laceliachicago.com/chicago-avondale-la-celia-latin-kitchen-food-menu
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Panaderia Nueva LeonDessertPilsenBakery - they have ice cream filled conchas$
http://panaderianuevoleonpilsen.com/
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J Parker Hotel Rooftop BarDrinksLincoln ParkHad a holiday party here - pretty lake views and good drinks.$$
https://www.jparkerchicago.com/
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Cafe TolaFoodLogan SquareI've only been to #4 but they have my fav. empanadas. Limited seating.$
https://www.cafetola.com/
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Cafe con LecheFoodLogan Square2nd favorite chillaquiles in the city$$
https://cafeconlechels.com/
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Cozy CornerFoodLogan SquareTraditional brunch spot with surprisingly deliecious chilaquiles.$-$$
https://www.cozycornerrestaurant.com/
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CarnivaleFoodWest LoopCame here for my first restaurant week - delicious food with a colorful and fun interior.$$-$$$
https://www.carnivalechicago.com/
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Small ChevalFoodLoop, Wicker Park
Au Cheval is the parent restaurant and is said to have the best burgers in Chicago - also doesn't accept reservations and heard it can take hoursto be seated so we go here! Classic burger place (think in n out but dif.)
$-$$
https://smallcheval.com/
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Lincoln LodgeComedyLogan Square
Nation's longest running independent comedy club - fun, low key vibes, with affordable drinks.
$
https://www.thelincolnlodge.com/
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Garfield Park ConservatoryMuseumWest Garfield
Beautiful garden conservatory with a fern room that will take you back to prehistoric times. Free for Chicago residents, $10 for non-resident adults
Free - $
https://garfieldconservatory.org/
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Asian Cuisine ExpressFoodLittle VillageFeatured on Netflix's Taco Chronicles, this place has the best al pastor!$-$$
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TacotlanFoodBelmont CraiganBest quesabirrias in Chicago!$-$$
https://www.tacotlan.com/
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ManchamantelesFoodBucktown
Upscale Mexican restaurant that specializes in mole - Chef Geno is so sweet and food is amazing!
$$ - $$$
https://www.manchamantelesrestaurant.com/
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Sazon CubanoFoodBucktownCuban restaurant - great sandwiches!$ - $$
https://www.sazoncubanocafe.com/
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Pastores and BrunchFoodLincoln squareCozy brunch spot serving American/ Mexican Food$ - $$
https://pastoresbrunchchicago.com/
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Rice N BreadFoodWrigleyvilleReally good Korean food and decent American diner food.$ - $$
https://ricenbread.com/
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SkydeckAttractionLoop (Downtown)
Check out the Chicago Museum before taking an elevator to the 103rd floor of the Willis (SEARS!) Tower for unmatched views of the city. Step onto the ledge and look down onto the street 1,353 ft below you!
$$-$$$
https://theskydeck.com/
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Nakama ToysShoppingLogan SquareA must see for all things anime, gundam, and more! $-$$$
https://www.nakamatoys.com/
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Wrigley FieldAttractionWrigleyville
Home of the Chicago Cubs. Catch a game at this iconic stadium if you get a chance. Or stop by the many bars and restuarants nearby!
$$-$$$
https://www.mlb.com/cubs/ballpark
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Jr.'s Red HotsFoodBucktown
Greasy spoon hut that's always there for you. Try an Italian Beef, Pizza Puff, Char Dog. or Lemon Pepper Tenders
$
https://share.google/dEgXjJks1Y8VsJSjw
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Alleycat ComicsShoppingAndersonville
Our favorite comic book store hidden in the Alley. Comics, figures, stickers, and more nerdy things
$-$$$
https://www.alleycatcomics.com/
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Navigator TaproomDrinksLogan Square
For the beer cconnoisseur. Pour your own drink by the ounce and get adventurous without commiting to a full glass. Free chips and bpardgames too.
$-$$$
https://navigatortaproom.com/
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Sushi TakuFoodVarious
All You Can Eat Sushi. Come hungry. A Japanese man on reddit said it's his favorite sushi in Chicago, and Victor feels the same way about the Wicker Park location.
$$
https://www.sushitaku.com/menu-locations/
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Maggie Daley ParkParkLoop (Downtown)Giant park in downtown that's great for families. Free
https://maggiedaleypark.com/things-to-do-see/play-garden/
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The 606ParkVarious
An abandoned rail line turned recreational trail and park named after Chicago's zip codes. Take a walk above the city while dodging runners, cyclists, and skateboarders.
Free
https://www.the606.org/
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Stay and Play Game CafeFood/Drinks/AttractionIrving ParkBoard games, Puerto Rican Food, and Drinks. Have fun! Famalies welcome. $-$$
https://stayandplaygamecafe.com/
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Stan's DonutsDessertVariousFamous Chicago donuts. $-$$
https://www.stansdonuts.com/
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