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Crowd of friends eating and talking at a Chicago street festival under the El tracks
ChicagoWeekendThings to doMaking friends
4 min read

Things to Do in Chicago This Weekend (and How to Find Plans)

A repeatable way to fill a Chicago weekend with things that put you near other people — plus the sources locals actually check on a Thursday night.

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Friends sitting on the sand at North Avenue Beach with the Chicago skyline behind them
ChicagoSummerSeasonalMaking friends
4 min read

Summer in Chicago: The Social Calendar, Month by Month

Chicago packs a year of social life into four months. Here is what happens when, and how to use the summer calendar to actually build a friend group.

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Neighbours talking outside a small café beside vintage apartment buildings on the Edgewater lakefront in Chicago
ChicagoEdgewaterMaking friendsNeighbourhood guide
4 min read

Making Friends in Edgewater: The Quiet Lakefront Neighbourhood That Rewards Regulars

Edgewater is vintage courtyard buildings, a beach at the end of the street and a commercial strip of small businesses that notice a second visit. It is the calmest place in Chicago to build a social life on purpose.

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People gathered on the grass beside the Humboldt Park lagoon and boathouse in Chicago at sunset
ChicagoHumboldt ParkMaking friendsNeighbourhood guide
4 min read

Making Friends in Humboldt Park: Where Chicago Still Does Things Outside

Humboldt Park has a 200-acre park with a beach, the Paseo Boricua, a serious music scene and some of the best cheap food in Chicago. Almost all of its social life happens in public — which is exactly why it is easy to join.

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Friends sitting on rocks by Lake Michigan at a Rogers Park beach in Chicago at sunset
ChicagoRogers ParkMaking friendsNeighbourhood guide
4 min read

Making Friends in Rogers Park: The Most Mixed Neighbourhood in Chicago

Rogers Park has beaches at the end of residential streets, more than eighty languages spoken in its schools, and rents that let you stay. It is the easiest neighbourhood in Chicago to belong to without knowing anyone first.

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Corner tavern and brick two-flats on a Bridgeport street in Chicago at golden hour
ChicagoBridgeportMaking friendsNeighbourhood guide
5 min read

Making Friends in Bridgeport: Chicago's Best-Value Neighbourhood for a Social Life

Bridgeport has corner taverns older than most Chicagoans, cheap rent, an artist community and a Sox game a walk away. It is the South Side neighbourhood where turning up twice is enough to be recognised.

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Tree-lined Bucktown street in Chicago with people walking on the 606 trail
LonelinessChicagoBucktownNeighborhoodsMaking friends
5 min read

Making Friends in Bucktown: The Quieter Half of a Loud Neighborhood

Bucktown sits directly north of Wicker Park with the same bones and half the noise. That makes it one of the easiest places in Chicago to become a familiar face.

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Historic Old Town Chicago street with brick townhouses and people walking at dusk
LonelinessChicagoOld TownNeighborhoodsMaking friends
4 min read

Making Friends in Old Town: Small Streets, Long Memories

Old Town is one of the oldest and most walkable neighbourhoods in Chicago, with a comedy scene, a summer art fair and enough small rooms to actually talk in.

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People sitting at communal tables in a Lincoln Square beer garden in Chicago
LonelinessChicagoLincoln SquareNeighborhoodsMaking friends
4 min read

Making Friends in Lincoln Square: The Neighbourhood That Still Has a Square

Lincoln Square has a pedestrian plaza, a folk music school, a summer festival calendar and beer gardens with communal tables. Structurally, it is one of the best neighbourhoods in Chicago for meeting people.

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South Loop Chicago high-rise skyline seen from the lakefront path with people walking
LonelinessChicagoSouth LoopNeighborhoodsMaking friends
4 min read

Making Friends in the South Loop: A High-Rise Neighbourhood You Have to Work

The South Loop has the lakefront, the museum campus and thousands of new neighbours in towers who never speak. Here is how to turn proximity into an actual social circle.

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Corner bar and low brick buildings on a quiet Ukrainian Village street in Chicago
LonelinessChicagoUkrainian VillageNeighborhoodsMaking friends
4 min read

Making Friends in Ukrainian Village: Chicago's Best-Kept Social Secret

Ukrainian Village has the neighbourhood bars, the old institutions and the walkability of Wicker Park without the queue. It is one of the friendliest places in Chicago to be new.

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