Unearth The Voyage
Chicago’s dining scene has earned global praise, but scoring a table at the city’s most sought-after restaurants can feel like winning the lottery. Reservations vanish in seconds, waitlists stretch for weeks, and even the savviest foodies struggle to snag a spot. Fortunately, with the right timing, flexibility, and a few insider tricks, you can beat the odds and experience these incredible culinary destinations.
1. Alinea (Lincoln Park)
Chicago’s legendary three-Michelin-star restaurant operates on a prepaid ticket system through Tock, making every release feel like a concert drop. New dates appear in batches, and prime Friday and Saturday evening slots disappear within minutes of going live.
Your best strategy is signing up for Alinea’s email newsletter and checking Tock regularly when new inventory launches. Mid-week dinners and later seating times around 9:30 p.m. tend to last longer than weekend prime slots.
Flexibility is your friend here—if you can shift your schedule by even one day, your odds improve dramatically. Patience pays off when chasing this culinary masterpiece.
2. Smyth (West Loop)
Tucked into the West Loop, Smyth has earned three Michelin stars with a constantly changing tasting menu that keeps diners coming back. The intimate dining room seats only a handful of guests each night, which means competition is fierce.
Reservations open on Tock in blocks, and you’ll want to be ready the moment they drop. Setting up alerts through Tock helps you catch new availability, especially for Tuesday through Thursday evenings when demand dips slightly.
Off-peak weekdays are your golden ticket if weekend plans don’t work out. Keep refreshing closer to your target date—cancellations do happen, and persistence can land you one of Chicago’s most coveted dining experiences.
3. Oriole (West Loop)
With two Michelin stars and a cozy, jewel-box dining room, Oriole delivers an unforgettable tasting menu that showcases seasonal artistry. Limited seating each night means reservations are a hot commodity, often gone within hours of release.
Oriole opens its books exactly 90 days in advance on Tock, so mark your calendar and be online at the precise moment. Late-evening seatings around 9 p.m. sometimes stick around longer than earlier slots, giving you a fighting chance.
Don’t forget to join Oriole’s official waitlist if your preferred date is sold out. Cancellations pop up regularly, and being on that list can turn a disappointment into a dinner you’ll never forget.
4. Ever (Fulton Market)
Curtis Duffy’s two-Michelin-star modernist restaurant in Fulton Market remains one of the toughest reservations in town. Ever’s innovative approach to fine dining has created a devoted following, and slots fill up fast across multiple booking platforms.
You can book through OpenTable or Tock via Ever’s website, and your best bet is aiming for Tuesday, Wednesday, or Thursday nights. Weekend tables vanish almost immediately, so weekday flexibility is key.
If you have a firm date in mind, start checking for cancellations about 48 hours before your target evening. Last-minute openings are surprisingly common as plans change, and a little stalking can reward you with an extraordinary meal.
5. Kyōten (Logan Square)
Kyōten brings an ultra-intimate omakase experience to Logan Square, complete with two Michelin stars and a chef counter that seats just a few lucky diners. Deposits and premium pricing keep the reservation book precise but perpetually packed.
Tock handles all reservations, and new dates drop periodically—you’ll want to monitor the platform closely. Single seats and less popular nights like Wednesday, Thursday, or Sunday offer better availability than Friday or Saturday.
Solo diners actually have an advantage here since the chef counter layout makes single seats easier to fit in. Flexibility with your dining day can transform an impossible reservation into an achievable reality at this exceptional Japanese gem.
6. Kasama (Ukrainian Village)
Kasama has become famous for its Filipino tasting menu, available only at dinner and released on a strict 45-day rolling calendar. Reservations drop at exactly midnight Central Time on Resy, and the entire month can sell out in minutes.
Set your alarm and be logged into Resy right at 12:00 a.m. when new dates go live. This midnight release strategy is non-negotiable if you want dinner—late arrivals find nothing but a waitlist.
The good news? Kasama’s daytime café operates on a first-come, first-served basis with no reservations needed. If dinner eludes you, the café still offers a taste of the restaurant’s celebrated Filipino flavors without the booking battle.
7. Monteverde (West Loop)
Sarah Grueneberg’s Monteverde has become Chicago’s pasta destination, with handmade noodles that draw crowds months in advance. Dinner reservations on Resy are routinely booked solid, making prime-time tables nearly impossible to snag.
Your secret weapon is lunch service, available Tuesday through Saturday and far easier to book than dinner. The bar area also operates on a first-come basis, offering walk-in access to the same incredible menu without the reservation headache.
Bar seating might mean a short wait, but it’s worth it for spontaneous pasta cravings. Lunch and walk-in bar spots let you experience Monteverde’s magic without planning weeks ahead or constantly refreshing Resy.
8. Rose Mary (Fulton Market)
Joe Flamm’s Rose Mary blends Italian and Croatian flavors in Fulton Market, creating one of the neighborhood’s most requested reservations. The restaurant’s popularity has only grown since opening, with weekend tables booked solid weeks out.
OpenTable manages all reservations, and you’ll want to book the instant new slots appear on the platform. Weeknight availability tends to open up faster than Friday or Saturday, so consider shifting your plans by a day or two.
Bar seating often has better availability and still gives you access to the full menu. Checking OpenTable regularly for cancellations can also pay off—people’s plans change, and their loss could become your gain at this Adriatic-inspired gem.
