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Luxurious Father’s Day Activities to Explore in Chicago

One of the benefits of an extended stay in a luxurious residence is that it can feel like your family’s home away from home. If you’re looking for something unique to do this Father’s Day, Chicago has endless possibilities for a memorable experience. From fine dining to personal shopping, you can make your dad’s day truly special.

Fine Dining

Swift & Sons

Swift and Sons main dining area

Dads love steak and if you’re looking for the most prime cut around, Swift & Sons is the place to go. Voted the #1 steakhouse in Chicago, Swift & Sons is located in a luxurious building that mirrors a turn of the century old boys’ club. Their house special beef Wellington for two is guaranteed to be worthwhile.

Swift & Sons
1000 W Fulton Market
Chicago, IL 60607

Devon Seafood Grill

sign outside Devon Seafood Grill

With an expansive selection of fish and steak downstairs and the Oyster Bar upstairs, Devon Seafood Grill hits the spot for fine seafood and drinks. Offering a three course special for Father’s Day, your dad will have a grand time dining on everything from Mini Lobster Rolls to Firecracker Shrimp.

Devon Seafood Grill
39 E Chicago Ave
Chicago, IL 60611

Grab a Drink

Cindy’s Rooftop

view of Cindy's Rooftop main dining area

If you want to experience one of Chicago’s best views, then look no further. Cindy’s Rooftop presents a relaxing environment where you can grab a drink and enjoy a panoramic view of Millennium Park, Lake Michigan, and other corners of the city. If you fall in the mood for exquisite dining, then grab a seat and join the staff to have dinner in the sky.

Cindy’s Restaurant
12 S Michigan Ave
Chicago, IL 60603

Revolution Brewing Taproom

Revolution Brewing main tap room

Located in Avondale just off the Kennedy Expressway, Revolution Brewing is the largest independently owned brewery in Illinois. They offer a wide selection of IPAs, lagers, and seasonal drafts which you can drink while sitting and chatting in their tap room. You can also join one of their complimentary tours of the brewery, a perfect activity for the beer lover in your family.

Revolution Brewing Taproom
3340 N Kedzie Ave
Chicago, IL 60618

The Sedgwick Stop

bar and stools at the Sedgwick Stop

If your father loves neighborly bars, then he’ll enjoy this spot just off the Sedgwick Brown Line. The Sedgwick Stop features craft beers, large whiskey selections, and friendly service. Everyone who stops off for a drink is sure to feel at home.

The Sedgwick Stop
1612 N Sedgwick St, Suite 3
Chicago, IL 60614

Update His Look

ESQ Clothing

esq clothing logo

For the best custom suit in Chicago, ESQ Clothing has you covered. Located in the West Loop, ESQ tailors handcraft suits to your specific needs. Select from over 40,000 variations of fabrics and they will design the perfect garment for your unique personality.

ESQ Clothing
555 W Jackson Blvd
Chicago, IL 60661

A Sharp Dressed Man

man in suit and tie

Perfect for men on any budget, these personal shoppers will pre-select items based on your size and taste when you call ahead to make an appointment. Once you show up to one of their locations, they will help you select the right outfit for any occasion. A Sharp Dressed Man also offers discounts for new clients.

A Sharp Dressed Man
516 N Ogden Ave, Suite 256
Chicago, IL 60642

Van Buren Gentlemen’s Salon

van buren gentlemen's salon reception area

If you really want to pamper your father, Van Buren Gentleman’s Salon offers everything from shoeshines to pedicures. Located on the edge of downtown’s financial district, they provide quick service and complimentary cold drinks because they know the modern man has things to do and places to be.

Van Buren Gentlemen’s Salon
235 W Van Buren St
Chicago, IL 60607

Local Events

Taste of Randolph Street

Located in the West Loop, this festival features live music, DJs, and samples of some of Chicago’s best food. Taking place on Friday June 15 — Sunday June 17,  the asking donation to enter is $10.  Some of the restaurants featured in the festival include:

    • Bar Siena
      outside seating area for Bar Siena
      Located in the heart of Chicago’s Restaurant Row, Bar Siena is a two story restaurant inspired by Italian street food. Brought to your table in small portions, their meals are intended to be shared among your family for a truly authentic Italian experience.
      Bar Siena
      832 W Randolph St
      Chicago, IL 60607
    • City Winery
      winery and main dining area
      If your father is a wine connoisseur, bring him to City Winery. Here he can indulge in a fine dining experience accompanied by live music from some of the greatest songwriters known today.
      City Winery
      1200 W Randolph St
      Chicago, IL 60607
  • Ronero
    main dining area for Ronero restaurant
    Spanish for “master of distilling rum” Ronero, is a new Latin restaurant specializing in rum cocktails. For a refined yet casual experience, their menu boasts impressive dishes centered on South American cuisine such as empanadas, lechon (cured pork belly), and pescado frito (Columbian fried whole red snapper).
    738 W Randolph St
    Chicago, IL 60661
    For the full list of restaurants and activities featured in the festival, click the link here.

Millennium Park Summer Film Series

outside movie theater at park

Presented at the Jay Pritzker Pavilion on Tuesdays at 6:30pm, guests can enjoy free admission to watch films in Millennium Park all summer long. Upcoming films for this month your dad might enjoy are:

  • Mad Max: Fury Road — June 12
  • Kinky Boots — June 19
  • Groundhog Day — June 26

Visit the city of Chicago’s full website for more information.