Chicago Restaurant Week: Where to dine in 2020

Chicago Restaurant Week: Where to dine in 2020

The 13th annual Chicago Restaurant Week (CRW), January 24 through February 9, features more than 400 restaurants including 350+ restaurants in the city and nearly 50 in the suburbs. 

CRW 2020 is the biggest ever. With so many restaurants and only 17 days to try them out at “bargain” prices it is important to choose carefully.

Specially curated prix fixe menus are set at $24 for brunch and lunch, and $36 and/or $48 for dinner (excluding beverages, tax and gratuity). 

You can try one of the 90 new restaurants participating in 2020 including: Offshore Rooftop and Bar (Streeterville), Tzuco (River North), Il Culaccino (McCormick Square), La Pizza & La Pasta at Eataly Chicago (River North), Cruz Blanca (West Loop), Indie Café (Edgewater), Mesler Chicago (Hyde Park), Queenie’s Supper Club (Near West Side) and Time Out Market Chicago (Fulton Market).

OR you can try, one or more of Show Me Chicago’s favorites listed here:

Where to dine

1. Tzuco

TzucointeriorMichelin-starred Carlos Gaytan formerly of Mexique is back in 2020 with a trio of eateries at 720 N. State in the former Roy’s space.

Tzuco was the first of the three to open in September 2019. Gaytan describes, Tzuco as a love letter to his homeland. The upscale menu is not what you typically expect to find in a Mexican restaurant. Gaytan’s unique and original dishes  feature Mexico’s imaginative flavors while connecting to the preparation techniques of French cuisine. Guests can partake in dishes showcasing bright ceviche preparations, steak tartar, delicate flavors of shrimp, clams, octopus, mussels, skate and salmon; and the richness of chicken tinga, pork, tortilla, rib eye and lentils – all brought together with the zest of aromatic spices and chile.

Chicago Restaurant Week at Tzuco

Why Tzuco: Because you’re not going to find food like this anywhere else
What: Dinner: $48
Menu and reservations

2. WoodWind

Duck tacos--a favorite at WoodWind. Photo: Carole Kuhrt-Brewer

Craving the duck for the duck tacos–a favorite at WoodWind. Photo: Carole Kuhrt-Brewer

Also debuting in 2019 was WoodWind that opened the former GreenRiver space at 259 E. Erie St. on the Northwestern Medical Campus.

The contemporary American menu, designed by Chef Matt O’Neill, combines regionally sourced and epicurean ingredients creating a playfulness to the cuisine that results in a whimsical and up-to-the-moment menu. Creative craft cocktails and an extensive wine list are also in the mix.

Both the menu and the atmosphere make this one of my favorites,

Chicago Restaurant Week at WoodWind

Why WoodWind: You’ll get a lot of bang for your buck with WoodWind’s CRW menu
What: Lunch $24; Dinner $36
Menu and reservations:

3. Cooper’s Hawk Esquirecoopershawkbar

For a place that’s built its reputation on wine, the Cooper’s Hawk flagship restaurant, also new in 2019, at 58 E. Oak St. can keep up with the big boys and girls on the end as well.

Chef Matt McMillin, a veteran of some of Chicago’s best including Carlos, Le Francais, Café Provencal and the Lettuce Group, has provided a broad spectrum of choices on  his 11-page menu.

Guest can choose from simple reasonably priced dishes to an elevated selection of upscale entrees including a Pistachio-Crusted Australian Rack of Lamb, a 25 oz Prime Bone-In Ribeye and Miso Glazed Chilean Sea bass–each paired with a trio of wine. 

Cooper’s Hawk Esquire Chicago Restaurant Week

Why Cooper’s Hawk: Because you’re going to love the tri-level space that provides a look at the history and traditions of wine
: Lunch $24, Dinner $36
Menu and reservations:

4. Offshore

The massive bar at Offshore. Photo: Carole Kuhrt-Brewer

The massive bar at Offshore. Photo: Carole Kuhrt-Brewer

If for no other reason, one should visit OffShore to experience the nation’s largest rooftop patio (according to the Guinness Book of World records) and the view.

Located on top of Navy Pier’s Festival Hall, the glassed in interior space and the massive outdoor patio provide a 360-degree view of what arguably is one of the best skylines anywhere.

Perhaps more of a bar than a restaurant, food is not left out in the cold at OffShore.

Helmed by Executive Chef Michael Shrader, the menu features small plates and shareables with a California accent focusing on seasonal, modern American cuisine with global influences.

Seating is casual. You can take a seat at the bar, high top tables or grab a comfy sofa.

PLEASE NOTE: OffShore can be a little tricky to get to in the winter–especially during the construction of the new hotel. Your best bet is to drive and park as far back in the Navy Pier parking garage as possible and then follow the signs. You can Uber, LYFT, or taxi using the address 1000 E. Grand. If you use a ride-share–know that an extra $5 will be tacked on–a tax from the city for “hard to get places” including McCormick Place and the airport–so give your driver a little extra–or walk across the street from the pier to the Lake Point Tower area and avoid the charge. There is also valet parking.

Head OffShore for Chicago Restaurant Week

Why OffShore: For the 360-degree view of the city
What: $24 Brunch, $36 Dinner
Menu and reservations:

5. Le Sud

Brown Butter ice cream made in house is a special treat at Le Sub. Photo: Carole Kuhrt-Brewer

Brown Butter ice cream made in house is a special treat at Le Sub. Photo: Carole Kuhrt-Brewer

Step inside this Roscoe Village gem at 2301 W. Roscoe St. and you’ll immediately be transported to the South of France, sans the vineyards and olive groves.

The vibe is warm and inviting featuring a stamped-pattern silver ceiling, exposed brick walls, yellow and red tones, ornate-framed mirrors, vases of sunflowers, wall-mounted dinner plates and chandeliers that resemble antique glass milk bottles. 

Le Sud’s authentic menu focuses on fresh, high quality ingredients, enhanced with modern techniques. All desserts are housemade.

Chicago Restaurant Week at Le Sud

Why Le Sud: For a trip to the South of France without the airfare and the Brown Butter ice cream
What: Dinner $36
Menu and reservations:


ROOH interior.

ROOH interior.

The highly-acclaimed Progressive Indian restaurant, ROOH, specializes in vegetarian and vegan fare featuring both a unique and elevated dining experience. ROOH opened late May 2019 inside the former Lunatic, The Lover, & The Poet space in the West Loop (736 W Randolph).

Diners can choose from large or small plates with dishes changing seasonally.

Those with a sweet tooth can choose from dessert options including Haji Ali Cream served with fresh mango and honey comb in a mango shell and Baked Semolina Cake with milk ice cream and toasted pistachio.

The cocktail menu showcases the spirit of Rooh with nine seasonal cocktails inspired by ancient Ayurvedic wisdom and its six tastes, or rasas – sweet, sour, salty, pungent, astringent and bitter.

For an upscale dining experience, put ROOH on your CRW menu.

Chicago Restaurant Week at Rooh

Why ROOH: For a one-of-a-kind experience
What: $48 dinner
Menu and reservations:

7. Terrace 16

Night city view from restaurant interior.

Night city view from restaurant interior.

Almost two years ago, Terrace at Trump rebranded itself with a new name, Terrace 16 (401 N. Wabash Ave.) and more budget friendly options.

Although the $16+ cocktails are still there, you can also scape by with a $7 Bud Light. I like to think of it as the place to go for a cheap drink with a Million Dollar view.

The food, too, has undergone a transformation with tweaks to the menu and lower prices.

The seasonal menu includes fried chicken (now with a Southern inflection, via pimento cheese and green-tomato relish) and the Terrace 16 burger is now simply the Terrace burger, with white-American cheese and “burger sauce” replacing the Gruyere and caramelized-onion toppings from the past.

The vibe is Chicago from the second to none city views to the creative cocktail menu that pays homage to Chicago landmarks including “The Trib” Tribune Tower; “It ‘s 5 o’clock Somewhere” Wrigley Building; the “Sun Times Old Fashioned” in remembrance of the Sun Times Building that formerly stood at that location and “Big Stan” for the Aon Building.

The service is above and beyond what you’ll find at many other establishments–on my recent visits, they have been willing to go the extra mile to please.

CWR at Terrace 16

Why Terrace 16: For the million dollar view and great service
$24 lunch/brunch $48 dinner
Menu and reservations:

8. Portsmithportsmighoysters3

If you are a fan of seafood, you can’t go wrong at Portsmith (660 N. State St.) in the Dana Hotel. For starters there’s not many places where you can get a 3-course seafood dinner for $36.

Secondly, thanks to their New England-raised Executive chef Nate Henssler, who has brought the ocean to Chicago, and created a fresh, seasonal menu.

Why Portsmith: For affordable fresh, seasonal seafood 
Brunch $24, Dinner $36
Menu and reservations:

9. Cabra


I put Cabra (200 N. Green St.) on my list for two reasons. First it is a “hot” Stephanie Izard property–the Girl and the Goat; The Little Goat, Duck, Duck Goat–all of which continue to be a must for foodies. And secondly, it’s the kind of place where you can easily spend more than you intend with the shareable plates–some of which are really too small to share. Think ceviche (pictured above) would you really want to share this?

Also, the Peruvian inspired spot, is the only one of Izard’s restaurants without “Goat” in the name or even a lot of goat on the menu. Or so I thought until reader Rebekah Ziesmer informed me that cabra means goat in Spanish. No surprise I got a C in high school Spanish.

CRW at Cabra

Why Cabra: For bragging rights without taking out a 2nd mortgage on your home
What: $24 Brunch,$24 Lunch, $48 Dinner
Menu and reservations

10. Bar Sótano

Laine Bayless. Photo: Carole Kuhrt-Brewer

Laine Bayless. Photo: Carole Kuhrt-Brewer

Hipsters will find themselves at home at Rick Bayless and daughter Laine Bayless’ Bar Sótano. The basement location, a former storage room under Frontera Grill ( 443 N Clark St), is a lot more than a bar.

But, the bar and Lanie are a big part of it. As spirits director Laine is always creating new cocktails based on her deep knowledge of agave spirits like tequila, mezcal and sotol.

The authentic Mango Chamoy served in a plastic bag. Photo: Carole Kuhrt-Brewer

The authentic Mango Chamoy served in a plastic bag. Photo: Carole Kuhrt-Brewer

The intimate 50-seat subterranean space simply stated is a Mezcal Speakeasy that focuses on agave cocktails and modern Mexican street food. The drinks are fun and authentic like the Mango Chamoy, pictured here, served in a plastic bag just the way you’d see it on a hot day on an Oaxcan street.

The street food menu is filled with a variety of unique offerings from Oaxacan Drinking Snacks – Oaxacan peanuts with red chile and garlic, avocado dip, chile mixe salsa, roasted chapulines (grasshoppers), crispy Oaxacan corn tlayudas. $10 (that pair well with the Mezcal heavy drink menu) to Charcutería where you can order a board of everything for $28. OR you can also order individually. The Mexican Paella, cooked to order, is a special treat.

CRW at Bar Sótano
WhyBar Sótano: Because it’s fun and authentic
$36 dinner
Menu and reservations:

11. Aboyeraboyer

Of my 12 recommendations for CRW, Aboyer (64 Green Bay Rd., Winnetka) is the only restaurant I haven’t visited (although I did make reservations for CRW). Nor have I been able to reach the George Trois Group.

I have added it based solely on its reputation–which to say the least is impressive.

According to its website, “Aboyer (ab-wah-yay) is a brasserie presenting a hybrid of American & French fare influenced by global flavors. ‘Brasserie’ is translated two ways — the first as the French word for ‘brewery’ & the second a type of French restaurant with a relaxed setting & professional service – Aboyer combines the latter with a touch of modern technique & atmosphere. Featuring refined French pub grub paired with both classic & mod-fusion craft cocktails, the space offers quick service in a nouveau brasserie-style with a soundtrack cultivated to match the ambiance.’

Aboyer does require a trip to the suburbs. The drive shouldn’t take more than 30 minutes pretty much wherever you are in the city (except way south) and the parking is easy once you arrive,

CRW at Aboyer

Why Aboyer: To find out what Aboyer means and why the restaurant was named that (Clue: it’s something that dogs do)
What: Dinner $48
Menu and reservations: 

12. Starbucks Reserve Roastery

The curving escalator--one of the many fun and unique touches inside. Photo: Carole Kuhrt-Brewer

The curving escalator–one of the many fun and unique touches inside. Photo: Carole Kuhrt-Brewer

I added Starbucks Reserve, the world’s largest Starbucks Roastery, that still has people standing in line on the Mag Mile to get into the 4-story space since it opened on a cold rainy day in October, 2019 because it’s fun.

Also the menu includes two signature cocktails in the price of dinner.

CWR at Starbucks Reserve

Why Starbucks Reserve: To see why people are still waiting outside in line 3 months after its opening
What: $48 Dinner
Reservations: no reservations will be taken–just come and hope for the best


For a complete list of participating restaurants and their curated menu offerings visit 


Best bets for 2019

Top 12 for 2018

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