Chicago: Best Time to Visit, May–Jun & Sep–Oct

When to visit.

Compare monthly weather

Historical monthly weather

Select a month to plan your visit.

WarmestJul · 79°F (26°C)

WettestMar

Best windowMay–Jun & Sep–Oct

Jan

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May

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Aug

Sep

Oct

Nov

Dec

Bar height: daytime high.Green underline: best window. Square outline: selected month.

Select a month for temperature, rainfall and modelled sunshine.

Weather data & source

2018–2023 averages, not a forecast. Wet days estimate days with at least 1 mm of rain or snow using a calibrated ERA5 threshold. Contains modified Copernicus Climate Change Service information. Weather data by Open-Meteo.com (AWS Open Data, CC BY 4.0). Sunshine measures daylight only. Open-Meteo

What to see

Start with the sights.

01What to seeHome Insurance BuildingExplore →

The Home Insurance Building was an early skyscraper that stood in Chicago from 1885 to its demolition in 1931.

02What to seeWillis TowerExplore →

The Willis Tower, formerly and still commonly referred to as the Sears Tower, is a 110-story, 1,451-foot (442.3 m) skyscraper in the Loop of Chicago, Illinois, United States.

03What to seeCloud GateExplore →

Anish Kapoor's mirror-polished Bean reflecting the skyline in Millennium Park.

04What to seeAon CenterExplore →

The Aon Center is a modern supertall skyscraper located in the Northeast corner of the Chicago Loop, Chicago, Illinois, United States.

05What to seeChicago RiverExplore →

The Chicago River is a system of rivers and canals with a combined length of 156 miles (251 km) that runs through the city of Chicago, including its center.

More sights (3)

Trump International Hotel and Tower

The Trump International Hotel and Tower, or simply the Trump Tower, is a skyscraper condo-hotel in the Near North Side community area in downtown Chicago, Illinois, United States.

Soldier Field

Soldier Field is a multi-purpose stadium on the Near South Side of Chicago, Illinois, United States.

Navy Pier

A lakefront pier of a Ferris wheel, boats and summer fireworks.

Where to eat

Where to eat in Chicago

Lou Malnati's Pizzeria

Chicago deep dish with a butter crust and the sausage laid in as a single patty. Going since 1971.

Manny's Cafeteria & Delicatessen

A Chicago institution since 1942, cafeteria-style with a corned beef sandwich that's a civic landmark. Politicians, cops, and everyone else line up under the fluorescent lights for the same reason.

Portillo's

The Chicago-style hot dog and Italian beef done at scale, since 1963, with a jukebox soundtrack and a line that moves faster than it looks. The gravy-dunked beef sandwich is the real order.

Girl & the Goat

Stephanie Izard's wildly popular West Loop small-plates room. The goat is a must.

Lou Malnati's

The definitive Chicago deep-dish: buttery crust and that famous sausage patty.

Smyth

Three-Michelin-star tasting menu built on hyper-seasonal farm produce.

Kasama

The world's first Michelin-starred Filipino restaurant: bakery by day, tasting menu by night.

Alinea

Grant Achatz's three-Michelin-star landmark: avant-garde dining that reshaped America.

Month by month

Chicago, month by month.

What to plan a trip around, month by month.

May in Chicago

Chicago in May. One of the best months to visit Chicago. Typical daytime highs around 66°F (19°C).

June in Chicago

Chicago in June. One of the best months to visit Chicago. Typical daytime highs around 79°F (26°C).

September in Chicago

Chicago in September. One of the best months to visit Chicago. Typical daytime highs around 75°F (24°C).

October in Chicago

What’s on in Chicago in October. One of the best months to visit Chicago. Typical daytime highs around 63°F (17°C).

Chicago Marathon

Make a plan

Before you go.

Transport, fares & local advice

Getting there

Fly into O'Hare (ORD) / Midway (MDW).

Know before you go

The L train connects both airports to downtown cheaply.
Deep dish is a tourist ritual, but locals love the tavern-style thin crust too.
The lakefront path is the best free thing in the city; walk or bike it.

On the map

Explore on Trailwind →View on Google Maps →

Questions

Frequently asked questions

When is the best time to visit Chicago?

The best time to visit Chicago is May–Jun & Sep–Oct, in United States.

Where is Chicago?

Chicago is in United States. The nearest major airport is O'Hare (ORD) / Midway (MDW).

What is Chicago known for?

Big shoulders, deep dish, and the greatest skyline debate.

Nearby on Trailwind

Beyond the city

When to visit.