Three separate holiday calendars cover Streeterville this year: the Magnificent Mile Lights Festival, Navy Pier's winter season and Chicago Shakespeare Theater's first-ever repertory run. Each one publishes its own dates. Put them side by side and most of the season lands on Saturdays. On three of those Saturdays, Nov. 21, Dec. 5 and Dec. 12, free fireworks over the lake and a chance to see two Shakespeare plays in one day happen within the same few hours.
The first of those Saturdays is also the biggest. Nov. 21 is Lights Festival day, the opening night of Navy Pier's winter fireworks and the first of Chicago Shakespeare's double-header days. Once you know how that day runs, the rest of the season through Jan. 3 is easier to plan.
Nov. 21, Hour By Hour
The Wintrust Magnificent Mile Lights Festival has a published schedule, and Navy Pier added its own event to the end of that night. Here is the day in order:
- 11 a.m. to 4 p.m. Lights Festival Lane runs at Pioneer Court, 401 N. Michigan Ave., with live entertainment, free Wintrust Photos with Santa and cheesecake decorating with Eli's Cheesecake. The 2026 performer lineup hasn't been announced yet.
- 5:30 p.m. The parade steps off at Oak Street and Michigan Avenue, led by grand marshals Mickey Mouse and Minnie Mouse from Walt Disney World Resort. As it moves south, it lights more than one million lights on 200 trees, block by block.
- Parade's end. The route finishes at Wacker Drive, just past the DuSable Bridge, according to Choose Chicago.
- 7:30 p.m. The Wintrust Fireworks Spectacular goes off over the Chicago River at Michigan Avenue.
- 8:30 p.m. Navy Pier's free Winter Fireworks open their season over the lake, with Wintrust presenting this first show.
That's two fireworks shows an hour apart, one on the river and one on the lake. The parade starts at the neighborhood's Oak Street edge and finishes at the river, so Streeterville sits on the east side of the whole route.
The same Saturday is also the first of Chicago Shakespeare Theater's double-header days, when you can see The Winter's Tale and A Midsummer Night's Dream back to back. The theater says it's the first time in its history that it has run two plays in repertory with a single company. That's 14 Chicago actors under Artistic Director Edward Hall, as part of its 40th anniversary season. On Nov. 21, The Winter's Tale starts at 7 p.m. in The Jentes Family Courtyard Theater on Navy Pier and runs 2 hours, 35 minutes plus intermission. If you're at that performance, you'll be inside the theater during both the 7:30 river show and the 8:30 lake show.
If you'd rather watch the parade from home, ABC7 Chicago airs it Sunday, Nov. 22, from 6 to 7 p.m.
The Saturdays That Stack
After Nov. 21, Navy Pier's fireworks repeat every Saturday through Dec. 26, at 8:30 p.m. according to the event page. Navy Pier's main events calendar has an older entry that says 8 p.m. starting Nov. 28, so check the event page before you head out on any given week.
Chicago Shakespeare lists four double-header days: Nov. 21 and 24, then Dec. 5 and 12. Three of them are Saturdays, the same nights as the fireworks.
| Date | Navy Pier Winter Fireworks | Chicago Shakespeare | Also happening |
|---|---|---|---|
| Sat., Nov. 21 | Season opener | Both plays in one day | Lights Festival, river fireworks at 7:30 p.m. |
| Tue., Nov. 24 | None | Both plays in one day | |
| Sat., Nov. 28 | Yes | Midsummer and Winter's Tale both in their runs | WonderFest's first weekend |
| Sat., Dec. 5 | Yes | Both plays in one day | WonderFest |
| Sat., Dec. 12 | Yes | Both plays in one day; last day of The Winter's Tale | WonderFest |
| Sat., Dec. 19 | Yes | Midsummer only | WonderFest |
| Sat., Dec. 26 | Final winter show | Midsummer only | WonderFest |
Dec. 12 is the last of the stacked Saturdays and the last day of The Winter's Tale, which runs Oct. 13 through Dec. 12 on Chicago Shakespeare's production page. After that, A Midsummer Night's Dream is the only play left, and it runs through Jan. 3. If you want to see both plays, you have until Dec. 12.
For anyone under 30, Chicago Shakespeare's 2026–27 season announcement lists a $30 Under 30 discount ticket program. Subscriptions start at $317 for a seven-play package.
What Thanksgiving Weekend Adds
The day after Thanksgiving, Navy Pier opens Wintrust Winter WonderFest in Festival Hall. It runs Nov. 27 through Jan. 3. Unlike the Saturday events, it's open daily except Christmas Day, so it fills the weekdays between those big nights.
The details from Navy Pier's event page and its 2026 announcement:
- Admission: $27 if you buy at least 24 hours ahead, or $32 within 24 hours or on the day. Children 2 and under get in free.
- Included: ice skating plus more than 10 indoor attractions, including a sparkling forest, the Cliffhanger and the Arctic Express Train.
- Add-on: a same-day Centennial Wheel ride for $10.
- Hours: opens daily at 10 a.m., with closing times that vary. Christmas Eve and New Year's Eve have holiday hours, and it's closed Christmas Day.
- Groups: discounted pricing for groups of 20 or more.
The $5 difference between buying a day ahead and buying the same day matters most on fireworks Saturdays, when people are most likely to decide to go at the last minute. If you're planning a WonderFest-then-fireworks evening for a group, buy the tickets the day before.
Dinner Between The Big Nights
A season packed with Saturdays means plenty of dinners on Michigan Avenue and the blocks just off it. Two newer spots are worth knowing.
The Infatuation added Mauro Mafrici Restaurant to its October new-openings coverage. It's a self-titled Italian restaurant from the former chef of the now-closed Pelago, at 980 N. Michigan Ave., Suite 230. The menu includes antipasti such as cuttlefish and octopus, pastas such as maccheroncini with lamb ragu and tortellini filled with ricotta and sausage, and dishes for four such as a timballo with duck sauce. Per The Infatuation, the restaurant only seats guests over 14 and asks diners to leave iPads at home, which is worth knowing before you book a family dinner around the parade.
A few blocks south, The Hand & The Eye at 100 E. Ontario St. opened to the public April 18, according to Block Club Chicago. It's a five-level magic and dining venue in the renovated McCormick Mansion. Eater Chicago listed its rooftop space, The Conservatory, as planned for fall 2026, with no opening date set. Eater also listed Esquire, a Japanese-influenced steakhouse with a 12-seat omakase club at 58 E. Oak St., for late fall. That address sits on the same Oak Street corner where the parade steps off.
For a quieter afternoon on one of the busy weekends, the Museum of Contemporary Art's Slow Dance features six artists, with performances in the galleries. It runs through March 14, 2027, well past the holidays.
After The Last Saturday
The last Saturday fireworks show is Dec. 26, but Navy Pier has one more. Its New Year's Eve Fireworks are set for 11:59 p.m. on Thursday, Dec. 31: a free, 10-minute show set to music. The same night, Navy Pier's events calendar lists a Whethan New Year's Eve concert in the Aon Grand Ballroom.
That leaves the first weekend of January. WonderFest and A Midsummer Night's Dream both close on Sunday, Jan. 3, 2027, so that's the last day for either.
For more about the neighborhood after the holidays, our Streeterville neighborhood guide covers the rest of the year, and our late-summer Streeterville guide covers the lakefront in warmer weather.
If you have family coming in for the Lights Festival, or friends asking which Saturday to pick, The Kelly Ladewig Group is happy to share what we know about the neighborhood. We'll put together a Streeterville evening that fits your group. Let's Go House Hunting whenever you're ready, and until then, enjoy the fireworks.
