Meaghan + CJ

August 30, 2025 • Chicago, IL
54 Days To Go!

Meaghan + CJ

August 30, 2025 • Chicago, IL
54 Days To Go!

Things to Do

Explore the Chicago Riverwalk!

The riverwalk is one of our favorite places in downtown Chicago. Enjoy a stroll (or run!), or stop by one of the many restaurants or bars. Our favorites are The Northman Beer & Cider Garden, Brews and Bites, and Tiny Tapp

Chicago Jazz Festival

Picture of Chicago Jazz Festival
Millenium Park

The headlining music artists have been announced for this summer’s Chicago Jazz Festival, taking place Aug. 28-31 in Millennium Park, along with Thursday opening-day events at the Chicago Cultural Center.

Headliners include the Grammy-winning vocalist Esperanza Spalding, pianist Monty Alexander, and trumpeter and vocalist Kermit Ruffins. Cuban guitarist and singer Eliades Ochoa will close the fest on Sunday night.

The annual fest over Labor Day weekend is programmed by the nonprofit Jazz Institute of Chicago and presented by the Chicago Department of Cultural Affairs and Special Events. A full lineup of concerts will be announced at a later date, including for the Von Freeman Pavilion stage, the WDCB Jazz Lounge, and the spotlight on young jazz artists at the Harris Theater Rooftop Terrace, all in Millennium Park.

All concerts are free; more information and artist updates at ChicagoJazzFestival.us.

Website

Chicago's First Lady

Picture of Chicago's First Lady
112 E Wacker Dr, Chicago, IL 60601, USA
(847) 358-1330

This river architecture tour is such a fun activity. It is run by volunteers from the Chicago Architecture Foundation and they do an incredible job explaining Chicago's amazing history.

The Art Institute of Chicago

Picture of The Art Institute of Chicago
111 S Michigan Ave, Chicago, IL 60603, USA
(312) 443-3600

No explanation required, the best museum in the city!

Field Museum

Picture of Field Museum
1400 S Lake Shore Dr, Chicago, IL 60605, USA
(312) 922-9410

Natural history museum that is great for young children