Chicago This Weekend and Next Week, Oct 16 to 25: Free Runway on State Street, Open House Chicago & the Celebrity Chef Ball

Chicago packs two of its best weeks of the fall into the next ten days. Runways move from Navy Pier to the middle of State Street, more than 200 buildings open their doors for free, Gordo and Metro go back to back at TAO, and the film festival runs every night until its closing gala. Then next Friday turns into the biggest food night of the season, with fifty chefs cooking for Meals on Wheels and twenty seats at a white truffle dinner, and Lil Yachty closes the run with a show the crowd helps program. Here is what to do in Chicago this weekend and next week, October 16 to 25, 2026, from free afternoons to black tie.

Friday, October 16: runway night at Navy Pier

The World Fashion Festival closes its Navy Pier run tonight at Bar Sol, 700 E Grand Ave, with seven designers from six countries walking the runway against the lake. Doors are at 5:30 PM, the show rolls into an after party, and the night runs until midnight. Tickets are $50, $75 and $100 on Ticket Falcon, and the higher tiers get you closer to the runway. Our World Fashion Festival guide has the full lineup.

For a quieter first drink, ride up to the 46th floor of the Four Seasons. Sip & Guzzle, the New York bar named No. 1 on North America’s 50 Best Bars in 2026, is pouring inside the Mile High Cocktail Club at 120 E Delaware Pl, Thursday to Sunday from 5 to 10 PM through March 14, 2027. The $85 seat includes two drinks from a rotating menu, split between precise sips like Drunk Grandma’s Apple Pie and big, fun guzzles like the Miami Vice Negroni. Seating is tight, so book on OpenTable. Read our Sip & Guzzle story before you go.

Saturday, October 17: a free day on State Street

The first Loop Arts Fest closes State Street to cars from Jackson to Madison, noon to 6 PM, and every stage is free. Twenty dancers from The Joffrey Ballet open the Second Stage at noon, Carpacho y Su Super Combo brings salsa and cumbia to the Main Stage at 3:45 PM, and Chicago soul singer Simone Green headlines at 5 PM. At 5:30 PM the World Fashion Festival takes its runway outside for a free show on the Second Stage, so if you missed Navy Pier, this is your seat. Food trucks, a beer garden and local artists fill the blocks between sets.

The same weekend, Open House Chicago opens more than 200 sites across 30 neighborhoods on Saturday and Sunday, October 17 and 18. It is free, and you just show up. This year’s first-timers include the Muddy Waters MOJO Museum in Kenwood, Smashed Plastic Record Pressing in Hermosa, the Blackhawks Ice Center and Broadway in Chicago’s Cadillac Palace Theatre. Check each site’s days and hours on openhousechicago.org and plan a route by neighborhood.

Saturday night: black tie at the Field Museum

The Women’s Board hosts the Field Museum Gala on Saturday, October 17, starting at 6:30 PM, celebrating the board’s 60th anniversary and honoring Marshall Field V. Stanley Field Hall after dark is one of the great party rooms in the city, and the gala raises money for the museum’s science and education work. Younger guests can enter through the Soiree, which flows into the main party for dessert and dancing. Tickets and tables are on the Field Museum Gala page.

Saturday, late: Gordo x Metro at TAO

When the gala crowd wants to keep going, River North has the answer. Gordo and Metro play back to back at TAO Chicago, 632 N Dearborn St, on Saturday, October 17, from 10 PM to 4 AM. General admission starts at $22.40 with fees, and the VIP table share, a seat at TAO’s communal table with bottles kept full all night, is $168 per person on the TAO tickets page. It’s 21 and over, and the dress code is smart casual to elegant: no shorts, baseball caps, athletic wear, tank tops, baggy clothing or flip flops.

All week: the Chicago International Film Festival

The 62nd Chicago International Film Festival runs through Sunday, October 25, with more than 100 features and shorts on screens across the city. Weeknights are the easy way in: pick a screening, then make a night of dinner nearby. The festival closes on October 25 with Tony Gilroy’s Behemoth!, starring Pedro Pascal and Olivia Wilde. Individual tickets are $26, and passes and the full schedule are at chicagofilmfestival.com.

Friday, October 23: the city’s biggest food night

The Celebrity Chef Ball takes over The Geraghty, 2520 S Hoyne Ave, on Friday, October 23, from 6 to 11:30 PM, with more than fifty chefs cooking a six-course dinner served tableside from thirteen chef stations. The night benefits Meals on Wheels Chicago, and tickets are $450. Rishi Kumar and Zubair Mohajir of Mirra lead the night, with teams from Topolobampo, Frontera Grill, Adalina, Tanta, Indienne and SIFR cooking alongside them. Our Chef Ball guide has the full roster.

Want something smaller that same night? The Alston, on the third floor of One Chicago at 750 N State St, sets just twenty seats for its White Truffle Dinner. The reception starts at 6 PM and dinner at 6:30, with five courses built around Alba white truffles and wine paired to every plate for $395 a person, prepaid on OpenTable. Our White Truffle Dinner story has the menu.

Saturday, October 24: Lil Yachty at Radius

Red Bull Setlist makes its U.S. debut at Radius Chicago, 640 W Cermak Rd, on Saturday, October 24, with Lil Yachty headlining and Chicago’s own Lyrical Lemonade on board. The twist is that fans help pick the songs, voting on which tracks from his catalog make the night, so no two Setlist shows sound alike. Doors open at 7 PM, the show is 18 and over, and tickets are sold through Radius and Red Bull’s event page.

Plan your ten days

• Fri Oct 16: World Fashion Festival, Bar Sol at Navy Pier, 5:30 PM to midnight, $50 to $100
• Thu to Sun: Sip & Guzzle at Mile High Cocktail Club, Four Seasons, 5 to 10 PM, $85 with two drinks
• Sat Oct 17: Loop Arts Fest, State St from Jackson to Madison, noon to 6 PM, free (World Fashion runway 5:30 PM)
• Sat Oct 17 and Sun Oct 18: Open House Chicago, 200+ sites, free
• Sat Oct 17: Field Museum Gala, from 6:30 PM
• Sat Oct 17: Gordo x Metro, TAO Chicago, 10 PM to 4 AM, from $22.40, 21+
• Through Sun Oct 25: Chicago International Film Festival, $26 per screening
• Fri Oct 23: Celebrity Chef Ball, The Geraghty, 6 PM, $450
• Fri Oct 23: White Truffle Dinner, The Alston, 6 PM, $395
• Sat Oct 24: Red Bull Setlist with Lil Yachty, Radius Chicago, doors 7 PM, 18+

Frequently asked questions

What is there to do in Chicago this weekend, October 16 to 18, 2026?

Start Friday at the World Fashion Festival at Bar Sol on Navy Pier, spend Saturday at the free Loop Arts Fest on State Street and Open House Chicago, dress up for the Field Museum Gala Saturday night, then dance until 4 AM at Gordo x Metro at TAO Chicago in River North.

What free events are in Chicago on October 17 and 18, 2026?

Loop Arts Fest fills State Street from Jackson to Madison with free music, dance and a World Fashion runway from noon to 6 PM on Saturday, October 17. Open House Chicago opens more than 200 buildings for free on Saturday and Sunday, October 17 and 18, with no tickets or registration.

When does the 2026 Chicago International Film Festival end?

The 62nd Chicago International Film Festival runs from October 14 to October 25, 2026. It closes on Sunday, October 25, with Tony Gilroy’s Behemoth!, starring Pedro Pascal and Olivia Wilde. Individual screenings cost $26, and passes and the schedule are on the festival’s website.

How much are tickets to the Celebrity Chef Ball in Chicago?

Tickets to the 2026 Celebrity Chef Ball are $450. The dinner is Friday, October 23, at The Geraghty, with more than fifty chefs cooking a six-course meal served tableside, and the evening benefits Meals on Wheels Chicago.

Where is the World Fashion Festival runway on Saturday, October 17?

On Saturday, October 17, 2026, the World Fashion Festival runway moves to the Second Stage at Loop Arts Fest on State Street, between Jackson and Madison, at 5:30 PM. The show is free, right after Simone Green’s 5 PM set on the Main Stage.

When is Lil Yachty’s Red Bull Setlist show in Chicago?

Red Bull Setlist featuring Lil Yachty is on Saturday, October 24, 2026, at Radius Chicago, 640 W Cermak Rd. Doors open at 7 PM, the show is 18 and over, and fans vote on the songs Lil Yachty performs, with Chicago’s Lyrical Lemonade joining the night.

Further reading

• World Fashion Festival tickets
• Loop Arts Fest schedule
• Open House Chicago sites
• Field Museum Gala
• Gordo x Metro at TAO Chicago
• Red Bull Setlist featuring Lil Yachty at Radius
• Chicago International Film Festival
• Sip & Guzzle at Mile High Cocktail Club on OpenTable

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