The month of May is off to a festive start with celebrations of both Cinco de Mayo and the 149th annual Kentucky Derby this weekend. With the renowned Louisville horse race on Saturday, and the high-energy Mexican holiday on Sunday, restaurants and bars all over Chicago are putting on epic parties to celebrate the occasions. 

Whether you’re a diehard Derby fan, looking to sip on a marg at a colorful fiesta, or want to experience a little of both, here are 23 places around the city to hit up this weekend.

Cinco de Mayo Fests

Cinco de Mayo and Tequila Tasting at Moe’s Cantina River North

Celebrate Cinco de Mayo all week from May 1 - 5 at Moe's Cantina in River North. This year Moe's is offering $30 margarita flights, $60 Patron towers, and $5 tacos every day, along with their usual happy hour deals. 

• Date: Wednesday, May 1 - Sunday, May 5

• Time: 4 p.m. - Close every day

• Location: 155 W. Kinzie St.

Cinco De Mayo weekend at Bodega Taqueria in River North

Bodega Taqueria in River North is celebrating Cinco De Mayo all weekend long from May 4 - 5 this year, with specials on draft and frozen margaritas, as well as Patron and Cazadores samplings on May 5. The event will also feature live entertainment, giveaways, and other fun filled activiites.

Date: May 4-5 p.m.

Location: 407 N Clark St

Cinco de Mayo at Carnivale

Step into the festive and colorful atmosphere of Carnivale without traveling across the globe. This West Loop favorite was Tripadvisor’s 2020 Travelers’ Choice Winner. Reservations are strongly recommended for this fiesta, which will include a live music, performances, and specials on Latin fusion cuisine, exotic cocktails, and one-of-a-kind desserts. 

• Date: Sunday, May 5

• Time: 2-9:30 p.m.

• Location: 702 W. Fulton Market

• Price: Free admission

Cinco de Mayo at Robert’s Pizza & Dough Company

Don’t miss Robert’s first-ever Cinco de Mayo pizza party featuring chicken tinga pizza, a specialty cocktail lineup featuring a margarita flight, and a live DJ. Make a reservation online.

• Date: Sunday, May 5

• Time: 5-8 p.m.

• Location: 465 N. McClurg Ct.

Cinco de Mayo Weekend at La Luna Restaurant

This Pilsen Mexican restaurant is hosting four days of festivities that will include live DJs and mariachi bands, drink specials, margarita towers, seltzer buckets, and special brunch offerings.

• Date: Friday, May 3 - Sunday, May 5

• Time: Times vary

• Location: 1726 S. Racine

• Price: Free admission

Cinco de Mayo Brunch Fiesta at Old Town Pour House

Join the fun at Old Town Pour House with their Cinco De Mayo Brunch Fiesta. For a $30 package includes access to a full brunch buffet complete with chilaquiles, breakfast tacos, a salsa bar, and more. Brunch packages will also include all margaritas.

• Date: Sunday, May 5

• Time: 10 a.m. - 2 p.m.

• Location: 1419 N. Wells St.

• Price: $30

Kentucky Derby Watch Parties

Kentucky Derby Watch Parties Presented by White Claw and Green Curtain Events

Watch the race in style and choose from premium indoor or outdoor packages for your group before tickets sell out at one of five locations. Admission includes a complimentary White Claw Hard Seltzer and giveaways.

• Date: Saturday, May 4

• Time: Times vary

• Locations: Bounce (Near North Side), Hubbard Inn (River North), Blüm Day & Nightlife (River North), Utopian Tailgate (Old Town), Roots Handmade Pizza (Printer’s Row), Barocina (Lakeview and West Town), Gold Coast Social (Gold Coast), The River Kitchen and Bar (Lake View East), and Paradise Park (Wicker Park)

• Price: Prices vary

The Annual Kentucky Derby Viewing Party at I|O Godfrey

Dress to the nines for this upscale watch party that includes contests for Best Dressed, Best Hat, and Best Couple. Reserve tickets to partake in one of their bourbon tasting classes, eat from a special Derby Day menu, and take pictures in the photo booth, all while watching the big race. 

• Date: Saturday, May 4

• Time: 12-8 p.m.

• Location: 127 West Huron St.

• Price: $30-$2,500

Vol. 39 Derby Day Celebration

Watch the race surrounded by timeless elegance while indulging in premium cocktails and gourmet chef-selected bites by Executive Chef Aaron Munson. Guests will receive a complimentary mint julep upon arrival and have the chance to participate in a best dressed campaign. A live bluegrass band will provide entertainment and guests can take photos in a vintage photo booth. Those who come in their best attire will have a chance to win Best Dressed and Best Hat competitions. Reserve tickets online.

• Date: Saturday, May 4

• Time: 3-7 p.m.

• Location: 39 S. LaSalle St.

• Price: $55

Cinco de Mayo + Derby Day Duos

Cinco de Mayo and Kentucky Derby Celebration at Time Out Market Chicago

Chicago's Time Out Market in Fulton Market will host its Kentucky Derby watch party on Saturday, May 4 and participate in a Best Dressed Contest. Specialty cocktails will be available from Whistlepig Bourbon and Rye along with exciting giveaways. Come back the next day on Cinco De Mayo for live entertainment and a special Tromba Tequila tasting.

• Date: Saturday, May 4 - Sunday, May 5

• Time: 4-7 p.m. (Friday), 11 p.m. (Saturday)

• Location: 916 W. Fulton Market

• Price: Free admission

Cinco de Derby Specials at Mac’s Wood Grilled

Dive into two days of all-day food and drink specials, including decadent options — like their delicious fajita platters — and discounted Coronas, Modelos, and Maker’s Mark Mint Juleps. On Saturday, watch the Kentucky Derby Undercard in the morning and the big event on 17 Ultra HDTVs that evening.

• Date: Friday, May 3 -Sunday, May 5

• Time: 11 a.m. Friday-2 a.m. Sunday

• Location: 1801 W. Division St.

• Price: Free admission