john philp
  • Home
  • Menswear
    • All Athletic Casual Formal staples
      Casual

      Bold Spring Jackets

      February 24, 2022

      Formal

      staples: the suit

      April 28, 2021

      Casual

      staples: the sneakers

      March 2, 2021

      Casual

      staples: the jeans

      February 1, 2021

      Athletic

      2021 Wellness

      January 14, 2021

      Athletic

      Better Sore Than Sorry

      June 20, 2020

      Athletic

      Runnin’ up that HILL (CITY!)

      October 31, 2019

      Athletic

      Breathe + Sweat

      January 16, 2019

      Casual

      Bold Spring Jackets

      February 24, 2022

      Casual

      staples: the sneakers

      March 2, 2021

      Casual

      staples: the jeans

      February 1, 2021

      Casual

      staples: the tee

      January 13, 2021

      Formal

      staples: the suit

      April 28, 2021

      Formal

      The Gift of Fit

      December 16, 2019

      Formal

      Kentucky Derby Weekend!

      May 9, 2019

      Formal

      Holiday Tux SZN

      December 22, 2018

      staples

      staples: the suit

      April 28, 2021

      staples

      staples: the sneakers

      March 2, 2021

      staples

      staples: the jeans

      February 1, 2021

      staples

      staples: the tee

      January 13, 2021

  • Travel
    • All City Guides Explore More
      Explore More

      Explore More: Caribbean Cruise

      January 31, 2023

      City Guides

      City Guide: Los Cabos

      January 21, 2023

      Destinations

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      Destinations

      Explore More: Holidays in London

      December 15, 2022

      City Guides

      City Guide: Los Cabos

      January 21, 2023

      City Guides

      Explore More: New York’s Best Bagels

      November 2, 2022

      City Guides

      City Guide: New York City (updated!)

      August 2, 2022

      City Guides

      City Guide: Stockholm

      May 25, 2022

      Explore More

      Explore More: Caribbean Cruise

      January 31, 2023

      Explore More

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      Explore More

      Explore More: Holidays in London

      December 15, 2022

      Explore More

      Explore More: Holidays in NYC

      December 6, 2022

  • Lifestyle
    • All Fitness Food + Drink Grooming Home Music
      Destinations

      Explore More: Holidays in London

      December 15, 2022

      Explore More

      Explore More: Holidays in NYC

      December 6, 2022

      City Guides

      Explore More: New York’s Best Bagels

      November 2, 2022

      Home

      Outer Space

      September 1, 2022

      Fitness

      2021 Wellness

      January 14, 2021

      Fitness

      Work(out) From Home

      March 24, 2020

      Fitness

      React, Run – Repeat!

      April 19, 2018

      Fitness

      Meet Morning Me

      January 16, 2018

      Food + Drink

      Explore More: New York’s Best Bagels

      November 2, 2022

      Food + Drink

      Old Fashioned Week – with a twist!

      November 9, 2018

      Food + Drink

      Swizzle into Summer

      July 20, 2018

      Food + Drink

      Bring on the New Year!

      January 3, 2018

      Grooming

      Hydrate Your Hair

      March 30, 2021

      Grooming

      Cut to the Classics

      December 11, 2019

      Grooming

      First Thing, Last Thing

      November 6, 2019

      Grooming

      The Right Stick

      May 7, 2019

      Home

      Outer Space

      September 1, 2022

      Home

      Home Furnishings

      July 13, 2022

      Home

      My (2nd) NYC Apartment!

      July 12, 2022

      Home

      Work(out) From Home

      March 24, 2020

      Music

      Build Out Your Gallery Wall

      February 3, 2022

  • By Destination
    • All Africa Asia Central America Europe North America Oceania
      Explore More

      Explore More: Caribbean Cruise

      January 31, 2023

      City Guides

      City Guide: Los Cabos

      January 21, 2023

      Destinations

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      Destinations

      Explore More: Holidays in London

      December 15, 2022

      Africa

      City Guide: Cape Town

      February 7, 2017

      Asia

      Explore More: Wuhzen, China

      March 30, 2017

      Asia

      Runnin’ Around: Hong Kong

      December 5, 2016

      Central America

      Explore More: Nicaragua

      May 2, 2018

      Europe

      Explore More: Holidays in London

      December 15, 2022

      Europe

      Explore More: Greek Islands (Spetses, Hydra, Paros, Antiparos & Sifnos)

      August 25, 2022

      Europe

      City Guide: Stockholm

      May 25, 2022

      Europe

      City Guide: Paris

      March 31, 2022

      North America

      Explore More: Caribbean Cruise

      January 31, 2023

      North America

      City Guide: Los Cabos

      January 21, 2023

      North America

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      North America

      Explore More: Holidays in NYC

      December 6, 2022

      Oceania

      Explore More: Byron Bay, Australia

      February 8, 2021

      Oceania

      City Guide: Sydney

      January 9, 2019

      Oceania

      Hawaiian Ways

      June 1, 2018

      Oceania

      Island Casual

      April 3, 2018

  • Shop The Locker
  • Home
  • About
  • Press
  • Contact

john philp

adventure & style seeker

  • Home
  • Menswear
    • All Athletic Casual Formal staples
      Casual

      Bold Spring Jackets

      February 24, 2022

      Formal

      staples: the suit

      April 28, 2021

      Casual

      staples: the sneakers

      March 2, 2021

      Casual

      staples: the jeans

      February 1, 2021

      Athletic

      2021 Wellness

      January 14, 2021

      Athletic

      Better Sore Than Sorry

      June 20, 2020

      Athletic

      Runnin’ up that HILL (CITY!)

      October 31, 2019

      Athletic

      Breathe + Sweat

      January 16, 2019

      Casual

      Bold Spring Jackets

      February 24, 2022

      Casual

      staples: the sneakers

      March 2, 2021

      Casual

      staples: the jeans

      February 1, 2021

      Casual

      staples: the tee

      January 13, 2021

      Formal

      staples: the suit

      April 28, 2021

      Formal

      The Gift of Fit

      December 16, 2019

      Formal

      Kentucky Derby Weekend!

      May 9, 2019

      Formal

      Holiday Tux SZN

      December 22, 2018

      staples

      staples: the suit

      April 28, 2021

      staples

      staples: the sneakers

      March 2, 2021

      staples

      staples: the jeans

      February 1, 2021

      staples

      staples: the tee

      January 13, 2021

  • Travel
    • All City Guides Explore More
      Explore More

      Explore More: Caribbean Cruise

      January 31, 2023

      City Guides

      City Guide: Los Cabos

      January 21, 2023

      Destinations

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      Destinations

      Explore More: Holidays in London

      December 15, 2022

      City Guides

      City Guide: Los Cabos

      January 21, 2023

      City Guides

      Explore More: New York’s Best Bagels

      November 2, 2022

      City Guides

      City Guide: New York City (updated!)

      August 2, 2022

      City Guides

      City Guide: Stockholm

      May 25, 2022

      Explore More

      Explore More: Caribbean Cruise

      January 31, 2023

      Explore More

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      Explore More

      Explore More: Holidays in London

      December 15, 2022

      Explore More

      Explore More: Holidays in NYC

      December 6, 2022

  • Lifestyle
    • All Fitness Food + Drink Grooming Home Music
      Destinations

      Explore More: Holidays in London

      December 15, 2022

      Explore More

      Explore More: Holidays in NYC

      December 6, 2022

      City Guides

      Explore More: New York’s Best Bagels

      November 2, 2022

      Home

      Outer Space

      September 1, 2022

      Fitness

      2021 Wellness

      January 14, 2021

      Fitness

      Work(out) From Home

      March 24, 2020

      Fitness

      React, Run – Repeat!

      April 19, 2018

      Fitness

      Meet Morning Me

      January 16, 2018

      Food + Drink

      Explore More: New York’s Best Bagels

      November 2, 2022

      Food + Drink

      Old Fashioned Week – with a twist!

      November 9, 2018

      Food + Drink

      Swizzle into Summer

      July 20, 2018

      Food + Drink

      Bring on the New Year!

      January 3, 2018

      Grooming

      Hydrate Your Hair

      March 30, 2021

      Grooming

      Cut to the Classics

      December 11, 2019

      Grooming

      First Thing, Last Thing

      November 6, 2019

      Grooming

      The Right Stick

      May 7, 2019

      Home

      Outer Space

      September 1, 2022

      Home

      Home Furnishings

      July 13, 2022

      Home

      My (2nd) NYC Apartment!

      July 12, 2022

      Home

      Work(out) From Home

      March 24, 2020

      Music

      Build Out Your Gallery Wall

      February 3, 2022

  • By Destination
    • All Africa Asia Central America Europe North America Oceania
      Explore More

      Explore More: Caribbean Cruise

      January 31, 2023

      City Guides

      City Guide: Los Cabos

      January 21, 2023

      Destinations

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      Destinations

      Explore More: Holidays in London

      December 15, 2022

      Africa

      City Guide: Cape Town

      February 7, 2017

      Asia

      Explore More: Wuhzen, China

      March 30, 2017

      Asia

      Runnin’ Around: Hong Kong

      December 5, 2016

      Central America

      Explore More: Nicaragua

      May 2, 2018

      Europe

      Explore More: Holidays in London

      December 15, 2022

      Europe

      Explore More: Greek Islands (Spetses, Hydra, Paros, Antiparos & Sifnos)

      August 25, 2022

      Europe

      City Guide: Stockholm

      May 25, 2022

      Europe

      City Guide: Paris

      March 31, 2022

      North America

      Explore More: Caribbean Cruise

      January 31, 2023

      North America

      City Guide: Los Cabos

      January 21, 2023

      North America

      Explore More: Best Tacos (& Margaritas!) in Austin, Texas

      January 7, 2023

      North America

      Explore More: Holidays in NYC

      December 6, 2022

      Oceania

      Explore More: Byron Bay, Australia

      February 8, 2021

      Oceania

      City Guide: Sydney

      January 9, 2019

      Oceania

      Hawaiian Ways

      June 1, 2018

      Oceania

      Island Casual

      April 3, 2018

  • Shop The Locker
City GuidesDestinationsNorth AmericaTravel

City Guide: Chicago

written by John Philp July 31, 2017

The Windy City, The City of Broad Shoulders, The Second City, Chi-town … one of my most requested city guides is finally here – Chicago! I’ve been living here for five years now and have seen the city change so much… restaurants have come and gone, the Cubs are now World Champions (what?!) but the pizza is still deeeeep. My friend Olivia and I decided to revisit all of our favorite spots over the past weekend to show you the best that Chicago has to offer! Chicago is situated on Lake Michigan, which gives the city an amazing beach-town feel in the summer filled with sailboats, BBQs, and hanging out along the lakefront. The prime time to visit the city is from June to September, and the favorite time of the year is October – when it’s a little brisk and the leaves start turning! Chicago can still be an exciting place in the winter but be warned that you’ll be bundled up pretty nicely and there might be just a little snow. Here are some hotels I’d recommend staying at:

  • Thompson Hotel
  • Public Hotel
  • The Langham
  • Soho House Chicago
  • The James
  • and for a more boutique stay, Hotel Lincoln.

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

The Food:

  • Cafe Ba-Ba-Reba! – Spanish tapas that’s great for big groups. my favorites: 43, 50, 30, 23, 32, 59, 62/52, 44
  • Green Street Smoked Meats (West Loop) – My favorite BBQ in Chicago… maybe because it’s Texas-style 😀
  • Girl & the Goat (West Loop)
  •  Little Goat Diner (West Loop)
  • Au Cheval (West Loop) – Best burger in the city,  but expect a long wait time!
  • Hubbard Inn (River North)
  • Sunda (River North)
  • ēma  (River North) – Light, California-inspired Mediterranean food. don’t forget the frozen Greek yogurt for dessert!
  • Big Star (Wicker Park)- Best tacos with the best patio in Chicago. Doesn’t hurt that they a killer margarita and full whiskey bar, too!
  • Drum Bar (Magnificent Mile) – my go-to cocktail bar, atop a boutique hotel
  • Duck Duck Goat (West Loop)
  • Crisp (Lakeview)
  • Avec (West Loop) – The best Mediterranean
  • Beatrix (River North/West Loop)
  • Summer House Santa Monica (Lincoln Park)
  • HUB 51 (River North) – breakfast nachos. enough said.
  • Antique Taco (Wicker Park)
  • Bongo Room (Wicker Park) – Indulgent brunch
  • Parson’s Chicken & Fish (Logan Square) – The patio = Chicago summer. A few frozen negronis (their house specialty!) and hush puppies and I’m the happiest person
  • Oiistar (Wicker Park)
  • 25 Degrees (River North/Wicker Park) – If you’d like to brunch – and use it as a verb – they’ve got $10 bottles of champagne.
  • Duck Duck Goat (Hong Kong-style Chinese)
  • Longman & Eagle (Logan Square)
  • Taxim (Wicker Park)
  • Lonesome Rose (TexMex in Logan Square)
  • En Hakkore (Bucktown)
  • Lilly’s Q (Wicker Park)
  • Aba (West Loop)
  • Monte Verde (Italian in West Loop)
  • Mott Street (Wicker Park) – Asian Fusion
  • Stan’s or Donut Vault has the best donuts.
  • Publican Quality Meats (West Loop)- The Chicken Parm #2 and Return of the Gyro might be the best sandwiches in Chicago. The new addition of their avocado salad is a great starter.
  • Parachute (Logan Square) – Funky-chic place serving modern, creative Korean-American fare plus wine & cocktails.
  • Giant (Logan Square) – Seasonal New American plates & craft cocktails are served in a funky storefront with local art

As far as Chicago deep-dish pizza goes, Pequod’s is my personal favorite… followed by Lou Malnati’s (on Rush St.!) — but my favorite pizza in town might be the cozy, underground  BRICKS. The Sweet Heat with some Slutty Ravioli can’t be topped! To get your fix of the famous Chicago hot dog, check out Devil Dawgs!

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

The Coffee: 

  • Buzz Killer Espresso
  • Gaslight Coffee Roasters
  • Caffe Streets
  • Ipsento Coffee
  • The Coffee Studio
  • The Wormhole Coffee – retro-themed shop in Wicker Park serving up Halfwit coffee
  • Big Shoulders Coffee – great grab-n-go in West Town
  • Intelligentsia Coffee – the Old Town location is my neighborhood coffee shop!
  • Sawada Coffee is right across from Soho House in the west loop and worth popping into..  get the Military!

Drinks:

  • DrumBar
  •  Violet Hour
  • Maude’s Liquor Bar
  • Lost Lake
  • Scoffloaw
  • The Dawson
MENSWEAR:
  • Independence
  • Una Mae’s
  • Stock MFG

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | UberTo Do: 

  • Cubs game at Wrigley Field (try seeing a game from the Wrigleyville Rooftops!)
  • Improv comedy show at Second City 
  • Chicago Water Taxi to Chinatown
  • Garfield Park Conservatory 
  • Architecture Boat Tour on Chicago’s First Lady  – It sounds dorky and touristy, but actually pretty awesome. This one is my favorite. If worst comes to worst, there’s a bar on board!
  • Cloudgate (‘The Bean”) in Millenium Park
  • Run/bike/walk along the Lakeshore Trail
  • Enjoy the room at the Signature Room at the John Hancock Tower – pro tip: go up there and sit at a table. don’t order, but take photos from the windows but then bail and go to Drum Bar across the street for even better cocktails and a more private space!
  • Shop along the Magnificent Mile 

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

Museums: 

  • The Museum Of Contemporary Art Chicago is one of the largest Post-WWII contemporary art museums in the country. The museum is filled with thought-provoking collections & installations and has hosted exhibitions ranging from Frida Kahlo to Jeff Koons. Located in Chicago’s Downtown.
  • With PoetryMagazine as its flagship initiative, the not-for-profit Poetry Foundation was created to promote poetry to a wider audience. Its 30,000-volume library contains rare and original works of modern and contemporary poetry. Located in Chicago’s River North neighborhood.
  • If you’d like a first-hand look at Chicago’s history, culture, and future, then make sure to stop by the Chicago History Museum. This engaging museum allows a peek into Chicago’s past. It houses many items and artifacts of Abraham Lincoln, including his deathbed, and even the clothing he and wife Mary Todd Lincoln wore the evening of his assassination. Located in Chicago’s Lincoln Park neighborhood.
  • This landmark building was the nation’s first free municipal cultural center. The Chicago Cultural Center hosts rotating galleries of art exhibitions and installations. The most notable of these was when a then-unknown (and now world-famous street photographer) Vivian Maier’s work was first exhibited in the United States. Fun fact: the center is also home to the largest Tiffany Favrile stained-glass dome in the world, measuring 38 feet in diameter. Located in Chicago’s Downtown.
  • Founded in 1903, the Adler Planetarium is America’s first planetarium. The building hosts three full-size theaters, intriguing intergalactic exhibits, and a collection of antique astronomy instruments. The Doane Observatory is the only place Chicagoans can view stars, planets, and celestial objects through the largest telescope in the Chicago area. It is located on Chicago’s Museum Campus.
  • The Shedd Aquarium was the first inland aquarium with a permanent saltwater fish collection and, at one time, was the largest indoor aquarium in the world. The aquarium contains over 1,500 species of fish, marine animals, and amphibians. It is located on Chicago’s Museum Campus.
  • One of the city’s most prominent museums, the Art Institute of Chicago is the second-largest art museum in the United States. The Art Institute houses impressive Impressionist and Post-Impressionist works in its permanent collection. The most notable pieces in the museum are a number of Claude Monet’s Haystacks and Water Lilies, Edward Hopper’s Nighthawks, Mary Cassatt’s The Child’s Bath, Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, and the iconic American Gothic by Grant Wood. And who can forget Ferris Bueller’s famous visit to the museum in the 1986 film! Located in Chicago’s Grant Park.
  • The architectural beauty that is the Field Museum was erected in 1921. The magnificent building is the focal point to Chicago’s  Museum Campus, and it’s no wonder why as the site attracts more than 2 million visitors every year. The Field Museum is also one of the nation’s most premier natural history museums in terms of collection size and its educational programs. Inside of its rich walls lives SUE, the most complete and well-preserved tyrannosaurus rex fossil discovered to date.

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | UberJohn Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

John Philp | Risky Jackal | Chicago Blogger | Menswear & Travel | Uber

I hope you found this guide helpful and informative! Please let me know if you are planning on visiting the city and have any other questions. Or recommendations! I know I couldn’t fit everything into here and sure I missed out on some great spots. Let me know if you’re an uber rider too ~ and if you used the ride request app to get around the city during your stay!

Stay Risky,

– John

Photography by John & Wesley Taylor 

City Guide: Chicago was last modified: January 28th, 2021 by John Philp
ChicagoCity GuideUber
0 comment
1
Facebook Twitter Google + Pinterest
previous post
The Perfect Summer Daiquiri
next post
My Nordstrom #NSALE Picks

You may also like

Explore More: Caribbean Cruise

January 31, 2023

City Guide: Los Cabos

January 21, 2023

Explore More: Best Tacos (& Margaritas!) in Austin, Texas

January 7, 2023

Explore More: Holidays in London

December 15, 2022

Explore More: Holidays in NYC

December 6, 2022

Explore More: New York’s Best Bagels

November 2, 2022

Leave a Comment Cancel Reply

About Me

About Me

Hey y'all! I'm John Philp Thompson, an NYC-based (but Texas born) photographer, model, blogger, list maker & risk-taker. I started this site as a destination for my city guides and to share some style tips along the way. I'm hoping to bring you all things menswear, travel, and fitness... and everything in-between!

Keep in touch

Facebook Twitter Instagram Pinterest Tumblr

Weekly Playlist

Recent Posts

  • Explore More: Caribbean Cruise

    January 31, 2023
  • City Guide: Los Cabos

    January 21, 2023
  • Explore More: Best Tacos (& Margaritas!) in Austin, Texas

    January 7, 2023
  • Explore More: Holidays in London

    December 15, 2022

Blogs I'm Digging

  • Captain Barto
  • He Spoke Style
  • Probably This
  • Scout Sixteen
  • sink the sun
  • The Healthy Camper
  • The Nathaniel Manual
  • The Northern Man
  • Tommy DiDario
  • Ty French
  • Ty Severe
  • We Travel For
  • Yummertime

Follow Me

Facebook

The Archives

  • January 2023
  • December 2022
  • November 2022
  • September 2022
  • August 2022
  • July 2022
  • May 2022
  • April 2022
  • March 2022
  • February 2022
  • November 2021
  • May 2021
  • April 2021
  • March 2021
  • February 2021
  • January 2021
  • December 2020
  • November 2020
  • September 2020
  • August 2020
  • June 2020
  • March 2020
  • December 2019
  • November 2019
  • October 2019
  • August 2019
  • July 2019
  • June 2019
  • May 2019
  • April 2019
  • March 2019
  • February 2019
  • January 2019
  • December 2018
  • November 2018
  • October 2018
  • September 2018
  • August 2018
  • July 2018
  • June 2018
  • May 2018
  • April 2018
  • March 2018
  • February 2018
  • January 2018
  • December 2017
  • November 2017
  • October 2017
  • September 2017
  • August 2017
  • July 2017
  • June 2017
  • May 2017
  • April 2017
  • March 2017
  • February 2017
  • January 2017
  • December 2016
  • November 2016
  • October 2016
  • August 2016
  • July 2016

john philp is proudly powered by WordPress