J. Graham’s Guide to Chicago
J. Graham’s Top 7 for People Somewhat Familiar with the City
- Boat the Chicago Architectural Tour Cruise — This is one of my favorites. With weather permitting, I recommend scheduling through the Chicago Architectural Foundation. This is the way to see downtown and gain insight to its history, mostly architectural history. You can also walk the River Walk downtown or schedule an architectural walking tour with the foundation. I do not recommend Navy Pier, which has the ferris wheel and is a small pennisula in downtown, but if you want or are able to venture on the lake on a boat via a tour agency or a boat-friend, that can be spectacular.
- Walk the Streets and Grab a Bite and Drink in Wicker Park / Bucktown — My primary residence for about 12 years of life. Wicker Park is a previous hipster / now significantly more gentrified arts, commercial, and food neighborhood in Chicago. Parts of the movie High Fidelity were filmed here. The neighborhood is easily accessible via the Blue Line on stops of Division, Damen, Western, or California. Milwaukee, Damen, and Division streets in the area have a wonderful assortment of restaurants, bars, cafes, and trendy shops. You can also walk or Divvy (Chicago’s bikeride share) the 606, which is an old rail line converted to a ~3 mile walking / biking path. Download the Divvy App on your phone or pay at the Divvy Station. Access the 606 near Damen and Wabansia streets or near Milwaukee and Wabansia by Ipsento 606 (coffee/cocktail shop) and just stroll east or west some blocks to see the neighborhood from a different angle. The further you go north-west on Milwaukee into Logan Square or Avondale, the more new / trendy / sparse / eccentric it gets. Logan Square has some amazing restaurants and bars along with a great boulevard and center square. Palmer Square can also be quite lovely on a nice day. Favorites in Wicker / Bucktown include Ipsento 606 (coffee and cocktails), Myopic Books (amazing used book store), Handlebar (Vegetarian / Pescatarian), Taqueria Chingon (taco spot on Western Avenue with great variety of tacos), Small Cheval (a great burger / fries / shake joint with nice patio and multiple locations in Chicago and daughter restaurant of Au Cheval in West Loop), Schwa (fancy BYOB and reservations required), Middlebrow (where J. Graham had a bachelor party meal with amazing breads and pizza in a hip environment), Stop Along (NY style pizza), Piece (New Haven style pizza), Cafe Istanbul, and many more. You can also jot down to the Ukranian Villiage about 1 mile away and see the Ukrainian Museum of Modern Art, have some Ukranian food or treats, and scope the churches or history museum nearby.
- See a Show at Second City or Elsewhere — Second City is where Bill Murray, Tina Fey, and a number of other famous actors and comedians started. It is a couple miles or so north of the downtown Loop area accessible via Red Line or quick-ish Lyft. I recommend ordering tickets and reserving seats before on the Second City website. Zanie’s downtown which is right nearby can also be great if you enjoy live comedy stand-up. (Pro Tip – Topo Gigio in Old Town before Second City for pre-show apps/dinner and wine). You should make reservations ahead of time. Also, be sure to Google Chicago shows before your visit as there are often great music and theater acts playing at the Historic Chicago Theatre Downtown, Chicago Symphony Orchestra, Steppenwolf, or elsewhere. If you want to do something off the beaten path, I highly recommend a jazz show at the iconic Green Mill up north accessible via longer Red line trip or seeing a show at smaller, iconic venues such as Empty Bottle (Wicker Park area) or Schubas (Lakeview area).
- Grab a Divvy and Bike the Lakefront — Divvy is Chicago’s bikeshare program. The lakefront area can be crowded but has bike paths without any car traffic. The views of the city and lake with the fresh air can make for a very pleasant and relaxing time to grab a little exercise, enjoy the people watching, and see the skylines. The Chicago downtown is beautiful and this is the best view of it from the ground. You can download the Divvy App ahead of time. I recommend grabbing a Divvy near Fullerton Street and the Lakefront if you are in the Lincoln Park area or somewhere near Navy Pier or at the Lakefront near Buckingham fountain downtown. You can also Divvy around the Museum District or neighborhoods if you are an experienced bike rider.
- Reserve or Wait for an Exquisite Meal in Chicago’s West Loop and Walk Randolph Area for a Beverage Beforehand — Some say it has died down a bit, but I still think the West Loop has amazing restaurants with a quick step just west of the downtown area. Chicago’s restaurants and foods are some of the best in the country and world. The West Loop is where many Michielan Stars live and the likes of Top Chef’s cook (e.g., Stephanie Izard, Rick Bayless, Beverly Kim, Paul Kahan). Reservations at least a month or two or more in advance are highly recommended. The meal can be very pricey, >$300, especially if you like to drink and eat a bunch, but should be memorable. A walk on Fulton or Randolph can be nice as a pre or post dinner view of the area.
- See a Game at Historic Wrigley Field — If you are a sports or baseball fan, Wrigley is amazing. It is easily accessible via the Red Line to the Addison stop. Even if you cannot see a game, it is worth visiting the stadium and surrounding neighborhood. It can be a little fratty and party heavy IMO but there are some fun and energetic areas if you are younger or just looking to have drinks, like Chicago’s classic Old Style, with arcade or bargames. Get off on the Belmont stop on the Red line before the Addison stop and walk-up 5-10 blocks north to Addison to get a feel for the Lakeview and Wrigleyville area. Sheffields on Shefield and School streets has a great beer selection and beer garden when the weather is nice. There is a Small Cheval near the stadium for burgers and fries, or Big Star for some midwestern-Mexican, and the area surrounding the stadium has really exploded over the years with a hotel, restaurants, DraftKings sports book, and other activities. Iconic sports bars such as Sluggers (with games inside) and the Cubby Bear surround the stadium. If you want to be different with a superb, upper-fast food joint, check out Indonesian spot Rendang Republic for an amazing duck dog or chicken plate.
- Explore Neighborhoods such as Andersonville, Lincoln Square, UpTown, Lincoln Park, Hyde Park, Pilsen, etc. — Chicago’s neighrborhoods are what give Chicago its life and vibe, so I recommend getting out of the River North, Loop, and downtown areas if you can. Andersonville, accessible via the Red Line and a bit of a walk to Clark Street, has some great shops with antiquing and thrifting (Cowboys and Astronauts) and bars/restaurants on Clark Street such as HopLeaf (one of J. Graham’s faves), Big Jones, Kopi Travellers Cafe (Vegetarian), Tala House (nicer with mex-med-American fair), Pizza Lobo, Bongo Room (Brunch Only) and M Henry (Brunch Spot). Stop by the Swedish American Museum for a quick 20 minute lesson on Chicago’s immigration history and a perfectly inner-chewy and outer-crisp, authentic Swedish pastry. Lincoln Square – Head north on Lincoln Avenue to Lincoln Square accessible via a longer Brown Line trip. The Brown Line ride from downtown to Lincoln Square, while long, offers great views of downtown and of the north neighborhoods in the city. Lincoln Square has dope restaurants and bars such as the Warbler, Gather, and Dancen (a Korean K-pop spot and one of one of J. Graham’s faves). If you have a craving for Thai or Vietnamese food, you can also check out the Argyle area in UpTown which is more off the beaten path but fun to mix it up to grab pho or pad thai. If you want to stay near downtown, head to Lincoln Park and visit the Lincoln Park Zoo, Nature Museum, and Conservatory, which can be combined with a Divvy on the Lakeshore or a tour before a show at Second City. This is a nice choice if you are with kids and a great way to see the parks and lakeshore.
Things you should probably do if it is your first or second time in Chicago
Explore the Bean / Grant Park / Millennium Park / Buckingham Fountain — If it is your first time in Chicago, this is sort of a must do. You can get a feel for the size of the city and architecture with views of the skyline.
Visit The Art Institute of Chicago — If you like art or art museums, I highly recommend the main art museum downtown in the Loop. It is accommodating to kids and has an international collection that rivals many. The lesser known Chicago Museum of Contemprary Art in Streeterville is also nice.
Check Out the Museum District — The Field Museum which is the Natural History Museum of Chicago is great as are the Shedd Aquarium and Adler Planetarium. Be prepared to wait in lines if you are visiting during the high seasons in early spring / summer / early fall. The Field, Shedd, and Adler are close to each other. The Museum of Science and Technology is great too but about 3 or so miles apart from the others, where you can also spend time in Hyde Park and Jackson Park area where U of Chicago is and Devil in the White City started.
Walk the Magnificent Mile — This is a pretty common and convenient thing to do just north of the loop / downtown on Michigan Avenue. There are lots of bougie / high-end shops and a big Starbucks. The walk gives you a feel for the breadth of the city.
Off the Beaten Path
Head to the Garfield Park Conservatory — More off the beaten path and certainly not a must do. This is a wonderful conservatory of beautiful plants in Chicago’s west neighborhood of Garfield Park open even in winter time.
Check out Chinatown —While Chinatown in Chicago is not as big as it is in New York or Los Angeles, it is a quick shot south of the loop. There are countless great Dim-Sum, Hot Pot and classic Chinese restaurants. Ping Tom Memorial Park is beautiful. Take the red line south to the Cermak-China-town stop and walk west past the Chicago Public Library Chinatown Branch and eat some Dim Sum or Hot Pot at a place in the square just a couple blocks west of the station. MingHin cuisine on Archer Avenue is my favorite Dim Sum.
Head to Pilsen for a Street Art Tour — Pilsen is a growing neighborhood just southwest of the Loop and accessible via the Pink line. There are a number of solid Mexican restaurants and picturesque street art. Thalia Hall has great ambiance for a music show with a dinner or drink in the hood beforehand.
Bike the Southlake Shore and scope Hyde Park or the Promenade — The Lakeshore path to south Chicago is less traveled and less touristy but offers amazing views and a nice reprieve from the city. During summer months, you can go swimming about 10 miles south on the promenade. You can walk around Hyde Park and see University of Chicago’s historic and beautiful campus where countless Nobel Prize winners studied. You can also check out South Shore Cultural Center where the Obamas got married. These places are a bit of a distance from each other but could be done in a day.
Lesser known Museum Visits — museums more off the beaten path that I would recommend for a rainy day or if you like museums include the International Museum of Surgical Science (a favorite near the lakeshore area in beautiful Gold Coast neighborhood), DuSable African History Museum, the American Writer’s Museum, Swedish American Museum, and Ukrainian National Museum and Museum of Modern Art. There are also a number of Frank Lloyd Wright houses and a Ernest Hemingway Museum in Oak Park, a west suburb of Chicago.
Places to Stay
There are hundreds of great hotels and places to stay in Chicago. It depends on where you want to be and how much you want to spend. Rates vary. An AirBnB in a neighborhood can be great for a group or longer-ish stay. I really have no firm recommendations. I have also only stayed in a handful of these places.
Known and more pricey places in the Loop include the Palmer House, the W, Raddison Blu, Chicago Athletic Hotel (where Cindy’s is located), the Langham and the Peninsula. River North / Mag Mile spots include the Drake and Hampton Inn. I used to stay in the Holiday Inn which is cheaper but great location with small but nice rooms in River North. If it is your first or second time and you want to see the sites, I recommend staying in the Loop or River North, closer to the Lakeshore. I would not stay in Navy Pier area as this is not accessible to the train. If you want to stay in a neighborhood, I would recommend Lincoln Park or Wicker Park. The Robey house in Wicker Park is a unique, European style boutique hotel very close to the Blue line and the Hyatt Place in Wicker is more common and casual. Hotel Lincoln is close to Lincoln Park and has easy access to the zoo and nature meuseum and lakeshore.
Places to Eat
Chicago has hundreds of great restaurants scattered throughout its various neighborhoods. It is the food capital of the US IMO and a lead food city in the world. I recommend making reservations for a night or two at least a month in advance to experience some of the more elegant and busy places. That said, if you are not a planner or you don’t like Foo Foo food, there are plenty of amazing places that simply do not take reservations. The most well known restaurants and restaurant areas are in the West Loop, River North, Wicker Park, and Logan Square. It is hard to go wrong.
You can simply search beforehand or upon arrival for spots. Infatuation Chicago does a decent job in rating places if you just want to find a place near where you are staying — https://www.theinfatuation.com/chicago; Top 25 Infatuation https://www.theinfatuation.com/chicago/guides/best-restaurants-chicago. You can also search by neighborhood or The Eater.
The spots from the TV show the Bear are all decent – https://www.choosechicago.com/blog/dining/chicago-locations-the-bear/
Some Top Restaurants
West Loop / River North
Au Cheval — Located in the West Loop, this restaurant does not take reservations but be prepared to wait several hours (2-3 hours during busy times) for a table on the weekend. You can put your name in at the front desk and then head elsewhere like Haymarket brewery next door for a drink while you wait. Au Cheval is known for its rich burgers and French american style foods. The bone marrow and bologna sandwich are also quite exquisite.
Next — This fine dining food experience is next level and from the same owners as Alinea (see below in Lincoln Park). It has amazing wines as well as crazy rotating menus. You have to buy tickets pretty well in advance. It’s a splurge at about $400 or so per person with a good wine pairing. You’ll spend your time talking about the food more than anything else.
Bavette’s — Located near River North, this is the top or one of the top steakhouses in Chicago. It is elegant but not too snooty in my opinion.
Monteverdi — Fancy Italian, pasta, and wine.
Avec — Smaller farm to table plates with solid selection of American foods. Not too busy on many days. A location in River North and West Loop.
Blackbird — Fancy small plate fine dining.
Sunny Gun — My wife said it’s nice.
Publican — Fun for large groups. More of a large food-hall with shared table seating, but is pretty great and its one of the few restaurants in the area that has lasted for so long. The chicken, carrots, oysters, and appetizers are solid.
Girl n the Goat — Stephanie Izzard’s premier restaurant in Chicago. It is good. It can get pricey. Duck Duck Goat is also good.
Aviary — If you like real fancy cocktails, make a reservation here. It is an experience. The Office is a speakeasy below for something more off the path. It is not exactly J. Graham’s style but it makes for a cool and memorable experience.
Timeout Market Chicago and Revival Food Hall — These are sort of unique spots to grab a bite with a similar vibe as a hawker center in the midwest.
Portillos — This is a chain unique to Chicago area, though it may be expanding. It is an upper-fast food spot, if you want a local bite of some Chicago classics. The Chicago dogs are great. The burgers are good too. If you are really looking for the Chicago experience, try the chocolate cake shake and be sure to have giardienara, a spicy pickled mix.
Billy Goat Tavern — iconic spot in River North. Burgers, no fries. That’s the way it’s been since the 1930s.
Lincoln Park
Alinea — This is an exceptional, fine dining restaurant and comes with a very hefty price tag requiring reservations several, several months in advance. If you love restaurants and love fancy food, this is about as good as it gets. 2 Michelin Stars in a quaint spot in Lincoln Park. Think the movie The Menu without the whole island / cult thing. Check here for full list of Michelins in Chicago – https://www.choosechicago.com/articles/food-drink/guide-to-michelin-star-restaurants-in-chicago/
Summerhouse Santa Monica — My wife like this. Cool atmosphere.
Topo Gigio — Italian and wine jawn that can be paired with a show at Second City in Old Town area.
Rendang Republic (Wrigleyville) — Amazing upper-fast Indonesian food, check out the duck dog or beef or chicken plate. Great for a deliciously quick-ish meal before or after a game or night out.
Pannes Bread Cafe (Lakeview) — This gem has been around the Lakeview / Wellington brown line for quite some time. It has delicious sandwiches, baked goods, and pastas that are perfect for a quick meal before a Cubs game or pre or post meal after a Lincoln Park conservatory, zoo, or nature museum hang.
Loop
Cindy’s Rooftop — Picturesque views of the city with pretty great food. Reservations recommended. It is an excellent place if you are staying downtown and want to have a meal with a view. Check out the game room in the Hotel for a more leisure, country club like vibe with billiards and cocktails.
Shaw’s Crabhouse — An old school Chicago feel with great atmosphere and food. Mostly seafood. The ambiance, decor, and wait staff is what makes this place a good choice for a Chicago experience. You can meet clients here or just have a fun, special family meal.
Wicker Park / Bucktown / Logan Square
Middlebrow — Brewey, winery, bread bakery with nice pizzas and hip / trendy atmosphere. Not very central in Wicker but a place to be seen among the hip folks. J. Graham bachelor party made a stop here with drinks at brewery Solemn Oath next door.
Small Cheval — Amazing fast-ish food – fries and burgers. This also exists in River North and Wrigleyville but this is the original one. On a nice day, you can eat on the patio and people watch in Wicker Park near the 606, a converted railway. J. Graham special – Go housestyle on your burger with garlic aioli and mustard with your fries and a chocolate shake. They changed the buns recently, which aren’t as good as the old ones, so —- if you can get to Bitter Pops in Roscoe Village, I highly recommend their smash-burgers as perhaps best in city, along with their extensive and excellent draft beer list. Their burger these days is now surpassing the more mass produced Small Cheval burger.
Lula Cafe — Smaller plates with a cool ambiance and good cocktails – Logan Square. Vegetarian-ish.
Longman and Eagle — Fancy gastropub in Logan. Ranked several years ago as a best new restaurant in the US by GQ. Good for a restaurant style burger and fries with a solid selection of drinks and bourbon.
Daisies — Handmade pastas – in Logan / Bucktown.
Boefhaus — Boutique steakhouse.
Table Donkey Stick — Germanic alpine fair. A staple of cheeses and exotic meats with excellent cocktails, ambiance, and wine selection. It’s been in the west side of Bucktown for 12 years and going strong.
Bake — It is a small and family ran bakery. I recommend the cookies as well as the scones and muffins. It is worth a stop by if you are in the neighborhood, though there are a number of excellent bakeries elsewhere. Sweet Mandy B’s is good as is Lost Larsen. The Swedish American Museum also does an authentic Chi-Swede pastry if you are in Andersonville.
Handlebar — It is a hipster, vegetarian / pescatarian place.
Pierogi Kitchen — This Polish food joint delivers an excellent Pierogi, Dill Pickle soup, and beer selection. Not too many people crave a pierogi on the daily, but this place delivers with its Polish authenticity. A great place to get a tad in touch with Chicago’s eastern Euro roots and typically not too packed. The proprietor also own Wurst Behavior, a Polish meat spot.
Drinks
Maplewood, Marz, Moody Tongue, Half Acre, Pipeworks, Dovetail, Begyle, Spiteful, Haymarket, and Piece are all popular local breweries. Piece also does great pizza in the Wicker Park area, though the beer is not the best. Most of the breweries have brew pubs you can visit. Macro breweries of Lagunitas, Guiness, Goose Island and other spots can be found not too far from downtown.
Cocktails – Plenty of speakeasys and fancy cocktail joints throughout the city. Violet Hour in Wicker Park and Aviary in West Loop are well known for ambience and mixologists. Three Dots and a Dash in River North and Billy Sunday’s or Scofflaw in Logan Square are also nice. Queen Mary’s in Wicker Park is a nice gin bar if that is your specialty. If you want the true Chicago experience, be sure to ask your bartender for a shot of Malort, Chicago’s refinely tasted liquor (or possibly a bug spray you can drink).
Wineries — Lots of restaurants have a solid selection of wines. Next in west loop and Giant and Table Donkey Stick in Wicker have great wine selections, as does Webster’s Wine Bar in Logan Square. There are no real local wineries. Bronzeville Winery is a great place on the soutside to grab a glass. Chicago Eater has a list. I only pretend to know wine. –https://chicago.eater.com/maps/best-wine-bars-chicago.
Pizza Contentions
I was previously the treasurer of Pizza Club Philadelphia before venturing to Chicago circa 2009. I brought my opinions and critiques of pizza from the east coast to the midwest during this transitional phase of my life. The pizza in Chicago has gradually caught up, and Chicago has a wide-range of amazing pizza establishments besides the most well known deep-dish.
Deep Dish – Chicago is world famous for its deep-dish pizza, though contended by Judge Scalia not to actually be pizza. Scalia on Pizza. J. Graham agrees on some levels with Judge Scalia (only on pizza), but if you are looking for the deep-dish experience, my recommendation is Pequods in the Lincoln Park-ish area. Giordanos, Lou’s, Gino’s, and Uno’s, the more well known deep-dish spots, are popular, great, and available throughout parts of the city.
Tavern Style – This style of pizza is having a renaissance in Chicago. J. Kenji Lopez-alt (one of J. Graham’s favorite chefs) recently did a tour of Chicago and its surrounding areas to write about Chicago’s tavern style and its history. Pizz’Amici is stellar and best thin za in city, perhaps country. Professor Pizza, near west loop and old town, ain’t bad and does a good tavern style. Go classic with Phils for the OG feel (Bridgeport – more off the beaten path) and a number of famous spots Chicago Eater on Tavern Pizza.
NY and Other Styles – Chicago’s water and bread is often not up to the standards of east coast cities like NY or Philly, but if you search for the right spot, you find something very comparable or sometimes even better. I recommend Stop Along (Wicker and Logan Square), Pizza Lobo (Andersonville or Logan Square – bocce ball and good for groups), Piece (New Haven style in Wicker – brewery and nice for groups), Spacca Napoli (Ravenswood – more traditional Italian style pizza), or Middlebrow (Logan /Wicker-ish – hip / trendy bread bakery, brewery, winery, pizza). Pizza Serio (Roscoe Village) delivers a solid pie and calzone with wood fire in little frills, solid beer, and a couple TVs for your pizza, weekend nostalgia.
We will save the whole is a wrap a sandwich debate for a different guide, which J. Graham brought attention to before this article That’s a Wrap
Other famous Chicago style foods include malort, giardiniera, hot beef sandwiches (see the TV show The Bear on Hulu), and Chicago dogs. Polish and Ukrainian foods are available with sizeable eastern European populations in surrounding areas west / north west. You can grab excellent Mexican, Italian, Ethiopian (Demerara Uptown), Japanese, Chinese, Argentinian, Middle Eastern, Indian, Greek, Turkish, French, Thai, and Vietnamese, among others, in certain neighborhoods.
36 Hours in Chicago –
A lot of what you can do and what you want to do depends on the weather and time of year in which you plan to visit Chicago. During high seasons of late-spring to early fall, I recommend walking or biking to various places and neighborhoods. During the cold winter months of December – March, I would recommend steering toward more indoor activities like museums and shopping areas.
For a two day trip, I would spend your first day exploring the grant park, art institute, and surrounding downtown area with a quick stroll on Magnificent Mile. You can grab lunch at Cindy’s downtown. You can make a reservation for around 7:00-7:30 in the West Loop (See spots above and elsewhere like Girl n the Goat, Avec, Duck Duck Goat, Publican, etc.). I would head to West Loop, Randolph Street area around 5:30 pm and pop in for a drink before dinner at a cocktail place or brewery. On the second day, I would schedule a Chicago Architectural Boat Tour and/or head out to a neighborhood of choosing, like Wicker Park, Lincoln Square, Andersonville or Lincoln Park. You can walk the streets and shops with a plan to do late brunch or lunch at a place of choosing in the neighborhood and perhaps a stop at a brewery or museum before going to an early show at Second City or elsewhere. You can do dinner before Second City in Old Town or Gold Coast area or make a reservation for after the show.
Every 5 years or so the NY Times releases a 36 hours in Chicago which is typically good. This is the most recent one released in September 2023. NY Times 36 Hours
SIDE TIPS – Download the Divvy App before if you plan to bike. Download the Ventra app before if you plan to ride public transportation. Chicagoans are generally very nice so do not hesitate to ask for directions. The entire city is on a grid with ground zero at State and Madison (e.g., 14 blocks north is 1400 N, 12 blocks west is 1200 W), so this can make it easy to understand where you are in the city.
Below is a map of the downtown public transit rail system known as the CTA (or the El – as it is an elevated train – think the movie the Fugutive), just to give you a feel. The train lines are colored and span much further than shown. Trains are generally reliable about every 2-7 minutes at normal times and 7-14 minutes at off hours, but recently there’s been more delays. The Red and Blue lines are the most often traveled. Red goes to Lincoln Park, Wrigley Field, Chinatown (South) and near Andersonville. Blue goes to Wicker Park, Logan Square and airport O’Haire. Brown goes to Lincoln Square as well as to Wrigley and Lincoln Park (Parallel to Red for parts). Take the Blue line into the City if you are arriving from O’Haire or Orange Line if you are arriving from Midway. It’s significantly cheaper, often faster than Lyft or Uber, and a nice time to decompress after a flight.

About the Author: I love travel, food, people, culture, history, innovation, evolution, anthropology, political science, economics, and, of course, providing advice (hopefully not too much unsolicited advice). The scientist in me brings curiosity and experimentation. The attorney in me brings pragmatism and opinions. My life travels include moving over 15 times before the age of 25 and visiting over 47 US states and 40 countries and counting. Anyways, I hope you enjoy my light-hearted guide about Chicago, my home for about 15 years. Leave a comment or contact me with questions. Be good. Safe travels.
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