Illinois is Chicago plus everything else: one of the biggest convention cities in the country, two airports, a summer festival calendar that never stops, and winters that change which side hustles make sense. Here are nine that pay in 2026.
1. Local Friend: show visitors Chicago, at your rate#
Most visitors see the Bean, the Magnificent Mile and an architecture boat. A Local Friend shows them the city the way a friend would, by the hour: Pilsen's murals and taquerías, Logan Square and Andersonville, the lakefront path, a Cubs game at Wrigley or the Sox on the South Side, deep dish versus tavern-style from someone with an opinion, how to use the L. You set your rate (commonly $25 to $45 an hour), Roavi lists you free and takes no commission, and the money is paid to you directly.
Chicago listings are still few, so a new profile is one of a handful and shows on the city pages immediately. No licence is needed for this; Chicago licenses sightseeing vehicles and their drivers, not someone showing a visitor around on foot. How it works in the US.
2. Rideshare at O'Hare and Midway#
Two airports, the convention traffic and the stadiums keep demand steady. After gas, $18 to $26 an hour, best at the airports, on convention weeks and on game nights. Winter surge helps if you can drive in snow.
3. Delivery#
DoorDash, Uber Eats, Instacart. $14 to $20 an hour after costs, noticeably better in winter when nobody wants to go out. Bike delivery works in the dense North Side neighbourhoods from spring to fall.
4. Tutoring#
Test prep for the selective-enrolment high school exams, the SAT and ACT, math and science, in Chicago and the North Shore and western suburbs. $25 to $60 an hour in person, less online.
5. Pet sitting and dog walking#
Rover and word of mouth. $30 to $60 a night for boarding, $18 to $28 a walk in Lincoln Park, Lakeview, the West Loop and the suburbs.
6. Notary loan signings#
Become an Illinois notary (application, bond and a short course, about $100 to $150), then a loan-signing agent. Each signing pays $75 to $125 and takes about an hour, evenings and weekends.
7. Convention and festival staffing#
McCormick Place is one of the largest convention centres in North America, and the summer brings Lollapalooza, the Taste of Chicago, Pitchfork, the Air and Water Show and a street festival most weekends. $18 to $28 an hour through staffing agencies, in bursts.
8. Spanish and Polish interpreting#
Chicago has one of the largest Mexican communities in the country and the largest Polish community outside Poland. Medical and legal interpreting pays $22 to $50 an hour, more with certification; phone interpreting works from home anywhere in the state.
9. Task and handyman work#
Furniture assembly, mounting, moving help and the annual May 1 apartment turnover. $30 to $55 an hour on TaskRabbit and Thumbtack.
What makes Illinois different#
The convention calendar, which makes event staffing and rideshare steadier here than in most cities. The seasons: summer is festivals and visitors, winter is delivery and indoor work. A minimum wage of $15 statewide, higher in Chicago, which sets the floor for hourly gigs. And a flat state income tax of 4.95 percent on top of federal and self-employment tax, so set aside 25 to 30 percent and pay quarterly on anything reported on a 1099.
Which fits your hours#
- Evenings and weekends with a car: rideshare, notary signings.
- Evenings and weekends without a car: tutoring, interpreting, Local Friend.
- Summer weekends: festival staffing, Local Friend.
- A few hours between things: delivery, dog walking, task work.
- You know your city and like people: Local Friend.
Starting as a Local Friend#
Free, ten minutes from your phone, three real photos, a review before you go live. Say which neighbourhood you live in and what you are good for; the specific profiles get booked.
Live in Illinois? Show visitors Chicago at your rate.
Become a Local FriendBy city: Chicago side hustles. Other states: New York, Texas, California. En español: cómo ganar dinero extra en Illinois.
Around the lake: Michigan. East: Ohio.
Frequently Asked Questions
What is the best side hustle in Illinois?
In Chicago, the ones tied to the convention calendar and the summer: event staffing at McCormick Place and the festivals, rideshare at O'Hare and Midway, and Local Friend, showing visitors the neighbourhoods beyond the Loop at a rate you set. For people with a skill, tutoring, interpreting and notary signings pay $25 to $125 an hour. Outside Chicago, tutoring, pet sitting, task work and delivery carry the list.How much can you make with a side hustle in Illinois?
After costs, typical 2026 ranges in Chicago: rideshare $18 to $26 an hour after gas; delivery $14 to $20; tutoring $25 to $60; pet sitting $30 to $60 a night; notary loan signings $75 to $125; event staffing $18 to $28; Spanish or Polish interpreting $22 to $50; task work $30 to $55; Local Friend at the rate you set, commonly $25 to $45. Downstate, roughly a quarter lower.How are side hustles taxed in Illinois?
Illinois has a flat state income tax of 4.95 percent on top of federal income and self-employment tax. Anything over $600 a year from one platform is reported on a 1099. Set aside about 25 to 30 percent and pay quarterly. Chicago has no separate city income tax.How does winter change side hustles in Chicago?
From December to March, outdoor and visitor-tied work slows and delivery and rideshare pay better because nobody wants to go out in it; tutoring and remote interpreting are unaffected. Summer is the opposite: Lollapalooza, the street festivals, the lakefront, Cubs and Sox season, and the visitors who come for all of it.What is a Local Friend and how does it work in Chicago?
Someone who lives in Chicago and shows visitors it by the hour: Pilsen, Logan Square and Andersonville beyond the Loop, the architecture from the river, a Cubs or Sox game, deep dish versus tavern-style from someone with an opinion, how to use the L. You set your rate, Roavi lists you free and takes no commission, and profiles are reviewed before going live. Chicago listings are still few, so a new profile is one of a handful. No licence is needed for this; Chicago licenses sightseeing vehicles and their drivers, not someone showing a visitor around on foot.