We’ve ridden the rattling L train around the Windy City in search of our favourite hotels, restaurants, shops, museums and more. Chicago is a welcoming city that brings together the best of many metropolises in the US – from the sandy beaches of Los Angeles and the neighbourhood feel of San Francisco to the vibrant culture of New York – with a dash of that famous Midwestern hospitality. We’re pulling into the station; hop on board.

Need to know

Get to grips with the basics

  1. Lake Michigan: In summer, residents flock to the 26 city beaches dotted along the fresh-water Lake Michigan’s shore, each of which has its own particular pull – from bars to volleyball.
  2. Baseball: There are two Major League Baseball teams in Chicago: the Cubs (who won the World Series in 2016) and the White Sox (who won in 2005).
  3. Transport: Chicago’s public transport revolves around the L train, which has eight lines and goes to just about every neighbourhood in the city.
  4. Etiquette: Chicago-style hot dogs, topped with yellow mustard, fried onions, relish, a couple of tomato slices, a pickle and a sprinkling of celery salt, are famous the world over. But don’t even think about asking for ketchup when you order.
  5. The Loop: Google “Chicago landmarks” and your search will throw up an array of skyscrapers mainly in and north of the Loop – the hub of big business and luxury shopping.

On sale now – part of the Monocle Travel Guide series

Watch the film


Hospitality at its finest

  1. Publishing House B&B, West Loop

    Fully booked

    Every detail in this beautiful city bolthole has been considered, from the fresh pastries in the butler’s pantry to the Malin+Goetz products in each en-suite bathroom.

  2. The Robey, Wicker Park

    Top drawer

    A celebration of Chicago’s architectural history, housed in a soaring wedge of a tower block from 1929 and the adjoining brick warehouse.

  3. Chicago Athletic Association Hotel, The Loop

    Be a sport

    This Venetian gothic marvel overlooks Millennium Park and was built in 1893 as a men’s club for the Chicago Athletic Association.


Local lingo

  1. The Bean: Nickname for Anish Kapoor’s “Cloud Gate”
  2. Dip: Word for “leaving”
  3. The L: The elevated train
  4. The Hawk: Cool breeze off Lake Michigan
  5. LSD: Lake Shore Drive

Food and drink

Smart bites and top stops

  1. Metric Coffee, Near West Side

    Serious about beans

    Swing by this mini Fulton Market café for a cup of coffee, a cold-pressed juice or simply to pick up a pack of ground beans to go.

  2. Baker Miller, Lincoln Square

    Morning munchies

    Baked goods are the name of the game at Baker Miller, where Dave and Megan Miller offer their delicious takes on morning favourites. The “famous” oatmeal earns that often overstated moniker: it comes with cultured cream, cinnamon-sugar pecans and a dollop of jam.

  3. Lost Larson, Andersonville

    Swede success

    This light-filled bakery-cum-café is devoted to Swedish-inflected dishes such as open-faced sandwiches stacked with pickled herring and lingonberry jam.

  4. Daisies, Logan Square

    Fresh from the farm

    The succinct menu at Daisies comprises handmade pastas (think beetroot agnolotti with dill), daily-changing starters and crowd-pleasers such as crispy fried mushrooms and cheese curds with buttermilk-tarragon dipping sauce.

  5. The Loyalist,West Loop

    Classy cocktails

    Tucked underneath John and Karen Shields’ fine-dining restaurant Smyth is The Loyalist, known for its well-made cocktails and killer burger. The bar’s Old Fashioned is an elegant variation on the classic, with maple and a dash of amaro for a hint of bitterness.


Shop talk

  1. Martha Mae, Andersonville

    Form and function

    Jean Cate set up her shop for art supplies and everyday tools in 2016. She makes the artwork lining the walls, as well as some of the ceramics.The maple and granite shelves are stocked with pieces by local makers such as Christie Chapin, plus Cate’s favourite international brands.

  2. The Dial Bookshop, The Loop

    Literary legacy

    Books sit on shelves made from 100-year-old bleacher wood sourced from a nearby basketball gym. The focus is on contemporary titles but you’ll also find vintage and rare tomes, plus small-press publications.

  3. Field & Florist, Wicker Park

    Garden variety

    Field & Florist operated as a flower farm and design studio for five years before opening this petite bricks-and-mortar outpost in 2017.Tucked away on the lower floor of an Italianate-style building erected in 1891, the shop is a slice of calm on busy Division Street.

  4. Gemini, Wicker Park

    Twice as nice

    French workwear by Vetra and traditional shirts by Portuguese Flannel brush shoulders with playful womenswear by Barcelona-based Paloma Wool and Swedish menswear by Our Legacy. Plus wall hangings, leather bags and many more “Made in Chicago” wares.


sign in to monocle

new to monocle?

Print magazine subscriptions start from £55.

Subscribe now






00:00 01:00

  • The Urbanist