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A guide to fun things to do in Chicago this weekend.

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Get smarter, faster on what matters in Chicago with Monica Eng, Justin Kaufmann, and Carrie Shepherd.

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Chicago celebrity quiz: Which stars are from Chicago?

Can you spot the celeb with Chicago roots?

History

First Illinois Trader Joe's unionizes

The Lincoln Avenue location is the fifth U.S. store to join Trader Joe's United.

Business

The <a class="gtmContentClick" data-vars-link-text="Trader Joe&#x27;s" data-vars-click-url="https://www.axios.com/2025/05/20/inflation-business-reputation-trader-joes-costco-arizona" data-vars-content-id="9abe3d81-05d9-4cb5-af6c-6c472178ea4b" data-vars-headline="First Illinois Trader Joe&#x27;s unionizes" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2025/05/20/inflation-business-reputation-trader-joes-costco-arizona" target="_self">Trader Joe&#x27;s</a> in Chicago&#x27;s North Center neighborhood just became the first location in Illinois to join the independent <a class="gtmContentClick" data-vars-link-text="union" data-vars-click-url="https://www.axios.com/2026/06/14/unions-ai-2028-elections" data-vars-content-id="9abe3d81-05d9-4cb5-af6c-6c472178ea4b" data-vars-headline="First Illinois Trader Joe&#x27;s unionizes" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2026/06/14/unions-ai-2028-elections" target="_self">union</a> of Trader Joe&#x27;s workers.Why it matters: One part of Trader Joe&#x27;s appeal, along with historically lower prices and unique products, is cheerful customer service. But union campaigns across the country in recent years have revealed that some Trader Joe&#x27;s workers aren&#x27;t as happy as they seem.

Darren Bailey's attack on Pritzker's yearbook sparks criticism

The Republican gubernatorial candidate mocked the governor's high school yearbook photos and captions.

News

Republican gubernatorial candidate Darren Bailey is facing criticism after attacking Gov. JB Pritzker over decades-old high school yearbook photos.The latest: Bailey <a class="gtmContentClick" data-vars-link-text="posted screenshots" data-vars-click-url="https://www.facebook.com/BaileyforIllinois/posts/pfbid027SeJgZSUJroM8r42HgVnR4cnYe2tn2yFFjS1hB6De5amUf1bKL4hsoYh6KkQmiUel" data-vars-content-id="4db38961-1d0b-42d6-a066-d1ebd3eb205c" data-vars-headline="Darren Bailey&#x27;s attack on Pritzker&#x27;s yearbook sparks criticism" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.facebook.com/BaileyforIllinois/posts/pfbid027SeJgZSUJroM8r42HgVnR4cnYe2tn2yFFjS1hB6De5amUf1bKL4hsoYh6KkQmiUel" target="_blank">posted screenshots</a> of Gov. JB Pritzker&#x27;s high school yearbook photos and captions. <ul><li>The yearbook photo shows Pritzker hanging with a friend, while the caption quotes F. Scott Fitzgerald and a list of what could be best described as &quot;senior quotes,&quot; which is standard in yearbooks. </li></ul>

Chicago's Naked Comedy Show pops up before Naked Bike Ride

The showcase will feature nude stand up comedy.

Things to Do

If Chicago&#x27;s yearly Naked Bike Ride floats your boat, you might appreciate a similar comedy concept rolling into town this week. The latest: The Naked Comedy Show is bringing its nude stand-up tour to Chicago for the first time Friday at <a class="gtmContentClick" data-vars-link-text="Crib Comedy Playspace" data-vars-click-url="https://thecribcomedy.square.site/" data-vars-content-id="d600a148-57e6-45a4-8503-0568edfe59d7" data-vars-headline="Chicago&#x27;s Naked Comedy Show pops up before Naked Bike Ride" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://thecribcomedy.square.site/" target="_blank">Crib Comedy Playspace</a> in East Garfield Park.

Chicagoans open French cottages in New Buffalo

The new cottage compound blends wellness and hospitality.

As someone who has rented summer homes in the Harbor Country area for decades, I was intrigued by the new <a class="gtmContentClick" data-vars-link-text="Petite Acres" data-vars-click-url="https://www.petiteacres.com/" data-vars-content-id="67435586-1052-45d9-9965-88cf93983274" data-vars-headline="Chicagoans open French cottages in New Buffalo" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.petiteacres.com/" target="_blank">Petite Acres</a> cottage compound in New Buffalo, which feels like a hybrid cottage, luxury hotel and summer camp.Background: Chicago couple Jeana Anderson Cohen and Justin Cohen dreamed up the facility after a 2020 trip to a resort in the south of France.

How to avoid traffic snarls this weekend

Hot spots include Andersonville, Humboldt Park, Burnham Harbor and Old Town.

Travel

Here&#x27;s our weekend traffic hot spots list.

How to avoid Memorial Day traffic in Chicago

Travel early in the morning on Sunday for the least traffic.

Holidays

Chicagoans leaving for <a class="gtmContentClick" data-vars-link-text="Memorial Day" data-vars-click-url="https://www.axios.com/2025/05/23/memorial-day-weekend-2025-federal-holiday-meaning" data-vars-content-id="896d46b8-6a3d-4c19-9cbf-00e3242579f1" data-vars-headline="How to avoid Memorial Day traffic in Chicago" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2025/05/23/memorial-day-weekend-2025-federal-holiday-meaning" target="_self">Memorial Day</a> roadtrips on Thursday or Friday afternoons will hit the worst traffic of the holiday weekend, per INRIX traffic data.The big picture: Despite soaring gas prices, <a class="gtmContentClick" data-vars-link-text="AAA is predicting" data-vars-click-url="https://www.ace.aaa.com/travel/advocacy/memorial-day-travel-forecast-safety-tips.html" data-vars-content-id="896d46b8-6a3d-4c19-9cbf-00e3242579f1" data-vars-headline="How to avoid Memorial Day traffic in Chicago" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.ace.aaa.com/travel/advocacy/memorial-day-travel-forecast-safety-tips.html" target="_blank">AAA is predicting</a> the <a class="gtmContentClick" data-vars-link-text="busiest Memorial Day ever" data-vars-click-url="https://www.axios.com/2025/05/12/memorial-day-travel-forecast-record-aaa" data-vars-content-id="896d46b8-6a3d-4c19-9cbf-00e3242579f1" data-vars-headline="How to avoid Memorial Day traffic in Chicago" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2025/05/12/memorial-day-travel-forecast-record-aaa" target="_self">busiest Memorial Day ever</a> for travel — making strategic timing essential.

Summer travel in Chicago: Flight cuts, rising fares and TSA delays expected

The summer outlook for Chicago flights is looking bleak.

The <a class="gtmContentClick" data-vars-link-text="summer outlook" data-vars-click-url="https://www.axios.com/local/chicago/2026/03/12/ohare-airport-capacity-faa-united-american-airlines" data-vars-content-id="4ffc48b8-c069-4026-ad64-ecb5991ea8e3" data-vars-headline="Summer travel in Chicago: Flight cuts, rising fares and TSA delays expected" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/local/chicago/2026/03/12/ohare-airport-capacity-faa-united-american-airlines" target="_self">summer outlook</a> for Chicago flights is looking bleak as rising fuel costs, FAA limits and security concerns squeeze air travel after a rocky spring. Why it matters: Summer is peak vacation travel season, when O&#x27;Hare&#x27;s already heavy traffic is pushed to its limits.

O'Hare Airport travelers face TSA shortages and ICE presence

Mayor Brandon Johnson said roughly 75 ICE officers were expected at O'Hare.

Travelers moving through <a class="gtmContentClick" data-vars-link-text="O&#x27;Hare " data-vars-click-url="https://www.axios.com/local/chicago/2026/03/19/chicago-airports-spring-break-travel-ohare-midway-faa-dhs" data-vars-content-id="b6f6cedc-59a9-4ee1-9640-32cf19cf5ec4" data-vars-headline="O&#x27;Hare Airport travelers face TSA shortages and ICE presence" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/local/chicago/2026/03/19/chicago-airports-spring-break-travel-ohare-midway-faa-dhs" target="_self">O&#x27;Hare </a>on Monday braced for long lines, <a class="gtmContentClick" data-vars-link-text="travel headaches" data-vars-click-url="https://www.axios.com/2026/03/23/travel-delays-shutdown-security-airfare-prices" data-vars-content-id="b6f6cedc-59a9-4ee1-9640-32cf19cf5ec4" data-vars-headline="O&#x27;Hare Airport travelers face TSA shortages and ICE presence" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2026/03/23/travel-delays-shutdown-security-airfare-prices" target="_self">travel headaches</a> — and the added uncertainty of ICE officers stationed at airport security.Why it matters: A partial government shutdown is straining airport operations nationwide — and hitting one of the country&#x27;s busiest airports at the start of spring break travel.

O'Hare, Midway brace for spring break crush amid shutdown chaos

The annual spring break for Chicago schools means a surge in traffic.

O&#x27;Hare and Midway are bracing for a spring break travel surge — just as delays and disruptions <a class="gtmContentClick" data-vars-link-text="pile up nationwide" data-vars-click-url="https://www.axios.com/2026/03/17/dhs-shutdown-tsa-fema-ice-democrats-discharge" data-vars-content-id="a9cf6a2c-0384-40c4-91f0-fddb3a8eb465" data-vars-headline="O&#x27;Hare, Midway brace for spring break crush amid shutdown chaos" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2026/03/17/dhs-shutdown-tsa-fema-ice-democrats-discharge" target="_self">pile up nationwide</a>.Why it matters: Chicago Public Schools&#x27; spring break is sending thousands more travelers through local airports at a moment when a prolonged federal shutdown is straining the system.

Chicago's Jibarito falls apart in Puerto Rico

The delicacy really disappoints due to a weird cheesy Salisbury steak-like filling.

Food and Drink

I recently spent a few days in Puerto Rico visiting family and eating lots of food including an island version of the Chicago-invented jibarito sandwich.Backstory: Humboldt Park restaurateur <a class="gtmContentClick" data-vars-link-text="Juan C. Figueroa started serving this steak sandwich " data-vars-click-url="https://www.chicagotribune.com/2003/06/18/saga-of-a-sandwich/" data-vars-content-id="0e5f1612-b18c-42e2-bbb9-a7da0fc016f0" data-vars-headline="Chicago&#x27;s Jibarito falls apart in Puerto Rico" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.chicagotribune.com/2003/06/18/saga-of-a-sandwich/" target="_blank">Juan C. Figueroa started serving this steak sandwich </a>using fried green plantain planks as bread in the mid-1990s at his Puerto Rican restaurant Borinquen.<ul><li>In the intervening decades it has spread to cities all over the country and even back to Puerto Rico, where I found it in San Juan&#x27;s old city at a spot called Restaurante el Jibarito or <a class="gtmContentClick" data-vars-link-text="La Fonda del Jibarito " data-vars-click-url="https://www.instagram.com/lafondadeljibarito/" data-vars-content-id="0e5f1612-b18c-42e2-bbb9-a7da0fc016f0" data-vars-headline="Chicago&#x27;s Jibarito falls apart in Puerto Rico" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.instagram.com/lafondadeljibarito/" target="_blank">La Fonda del Jibarito </a>depending on which sign at this location you follow.</li></ul><figure><img alt="Left: Woman with glasses holding a plate of food inside a restaurant with a Puerto Rican flag wall. Right: Green exterior wall of Restaurante El Jibarito on a colorful street with cars parked." height="1080" id="a0346c75-ee2b-46e5-b96d-b4890c61c93e" src="https://images.axios.com/w39zcR527o3o44m4dqD0Z7BrLTU=/2026/03/09/1773065919984.jpeg" width="1920" srcset="https://images.axios.com/WY_SzVl1r2J1viypNAJBte5m_9s=/0x0:1920x1080/1920x1080/2026/03/09/1773065919984.jpeg?w=1920 1920w, https://images.axios.com/Lq7ArmfKvHEgas2GJTjaH-ky38M=/0x0:1920x1080/1600x900/2026/03/09/1773065919984.jpeg?w=1600 1600w, https://images.axios.com/WRH7ce1lMiyMabZptBvWW7t5InY=/0x0:1920x1080/1366x768/2026/03/09/1773065919984.jpeg?w=1366 1366w, https://images.axios.com/sHK6Zrt5Thn_YIjFQ7BIOANDYfE=/0x0:1920x1080/1024x576/2026/03/09/1773065919984.jpeg?w=1024 1024w, https://images.axios.com/KQxgbgz5ywARnooHQY5Nel_v0KU=/0x0:1920x1080/768x432/2026/03/09/1773065919984.jpeg?w=768 768w, https://images.axios.com/2_lO70t6xqE-X2nzI2PYi4ocC0Q=/0x0:1920x1080/640x360/2026/03/09/1773065919984.jpeg?w=640 640w, https://images.axios.com/Pur9pvPkipzWfNvOMw-9pfrd9x8=/0x0:1920x1080/320x180/2026/03/09/1773065919984.jpeg?w=320 320w"/><figcaption>Monica holds the Puerto Rican version of a Jibarito in San Juan. The exterior of Restaurante el Jibarito/La Fonda del Jibarito in San Juan&#x27;s old city. Photos: Monica Eng/Axios </figcaption></figure>The sandwich: Disappointing. The plantain planks came out broken and filled with — not ribeye, pork or any of other Chicago faves but — some weird cheesy Salisbury steak for $19.95.<ul><li>Yes, but the sandwich does come with a tasty trifongo (breadfruit, plantain and yuca fritter) on the side. Has anyone ever seen this in Chicago?</li></ul>The bottom line: When trying &quot;Chicago treats&quot; in other cities, I often brace for the worst but here I expected something better.<ul><li>I guess we can chalk it up to another delicacy Chicago does better than any other place in the world.</li></ul>

Chicagoans caught in narco violence in Mexico

Sunday night at least eight continue to shelter in place after car jacking and bombed car.

At least eight Chicagoans were sheltering in place in Puerto Vallarta on Sunday amid violent attacks throughout the region in response to the capture and death of the Mexican <a class="gtmContentClick" data-vars-link-text="cartel leader" data-vars-click-url="https://www.axios.com/2025/12/09/trump-mexico-colombia-venezuela-strikes-maduro" data-vars-content-id="0620688d-d624-485a-9556-6d28b5f1f789" data-vars-headline="Chicagoans caught in narco violence in Mexico" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2025/12/09/trump-mexico-colombia-venezuela-strikes-maduro" target="_self">cartel leader</a> known as &quot;<a class="gtmContentClick" data-vars-link-text="El Mencho" data-vars-click-url="https://www.axios.com/2026/02/23/mexico-cartel-leader-el-mencho-drug-lord-killed" data-vars-content-id="0620688d-d624-485a-9556-6d28b5f1f789" data-vars-headline="Chicagoans caught in narco violence in Mexico" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2026/02/23/mexico-cartel-leader-el-mencho-drug-lord-killed" target="_self">El Mencho</a>.&quot;Zoom in: Lakeview resident Jonathan Pizer tells Axios that he and his husband Brad Lippitz were heading to go whale watching with two Chicago friends Sunday morning when their car was stopped.

Travel's newest flex: "Skillcations"

72% of people want time off work to explore a personal passion, Hilton's 2026 trends report found.

In 2026, <a class="gtmContentClick" data-vars-link-text="vacations" data-vars-click-url="https://www.axios.com/2025/12/23/2026-vacation-holidays-pto" data-vars-content-id="4092dab8-936c-47ba-b758-117bda09eee0" data-vars-headline="Travel&#x27;s newest flex: &quot;Skillcations&quot;" data-vars-event-category="story" data-vars-sub-category="story" data-vars-item="in_content_link" href="https://www.axios.com/2025/12/23/2026-vacation-holidays-pto" target="_self">vacations</a> aren&#x27;t just about switching off — they&#x27;re about coming back smarter. Why it matters: Vacations are being redefined as investments in personal growth — a shift that&#x27;s reshaping how people use PTO and how the travel industry sells time away.

How to beat Illinois traffic this Thanksgiving

Avoid gridlock with travel advice for the busiest Thanksgiving week on record.

Culture

Thanksgiving&#x27;s almost here and AAA is expecting a record 4.1 million Illinoisans to travel at least 50 miles over the next six days.Why it matters: Record holiday trips could bring heavy holiday traffic. So we&#x27;ve gathered some data to help you do more chewing and less stewing, more baking and less braking, more memory sharing and less highway swearing. OK, we&#x27;ll stop.

ð¨ Weekend traffic alert  for June 12-14, 2026

Data: Chicago Office of Emergency Management and Communication; Chart: Monica Eng/Axios

A table that shows Memorial Day weekend 2026 road traffic forecasts by day. Worst driving windows are Thursdayfrom noon to 9pm, Friday from 11am to 8pm, Saturday from noon to 5pm, and Monday from noon to 5pm.