Taylor's Tip

Elevate your dinner with a sommelier service. Do NOT skip out on the bread service! Any of the options are incredible! Valet parking is offered or you can reserve a spot with SpotHero. The Amalfi Lemon Linguine took me straight back to the Amalfi Coast– definitely my recommendation! Enjoy the gorgeous riverwalk after dinner, maybe grab dessert at Sweet Home Gelato if you didn’t already order some here!

Taylor's Tip

Crowd-pleasing modern Jewish deli in the Loop with plenty of options for everyone. Even things for vegetarians like the Veggie Reuben or the Eleven Impossible burger! Perfect spot to grab lunch before or after heading to the Shedd Aquarium.

Taylor's Tip

$15 valet parking is offered on site if you drive, but this is certainly walkable! If you want to enjoy the games and dine at the same time, only one reservation needs to be made. Book a private bowling alley or bocce ball round for fun after dinner!

Taylor's Tip

The most amazing salad bar you’ll ever come across! Don’t miss it! Right next to Lincoln Park Zoo, making at a great option for dinner after an afternoon with the animals!

Taylor's Tip

Located in Lincoln Park– lots of shopping close by to walk around to after lunch, or you could walk over to the lakefront! Check out the happy hour 4PM-6PM daily in the bar area! If you have a group, tapas is always a great choice that everyone can share and keeps things on the lighter side!

Taylor's Tip

If you get a chance to go during the holiday months, they have fun festivities with whimsical decor! This is by far one of, if not the best, rooftop spots in Chicago right next to the river with incredible views A picturesque spot to celebrate since it is a unique, one of a kind, memorable place, just like your milestone or celebration is! Walkins are accepted, but may be a long wait. Reservations are recommended but book months in advance, so plan this early on! The Smoke Show cocktail is *chefs kiss*.

Taylor's Tip

Valet parking is offered, cash only, in front of the restaurant. Otherwise I recommend ride share.

Taylor's Tip

Absolute perfect spot for delicious cocktails to help revive you after a night out! I recommend going for brunch but they do offer a kids menu as well!

Taylor's Tip

You wouldn’t expect it from the looks, but their pizza is amazing! I recommend the Tony for something different & the Tim for classic with a Chi twist. They offer bottomless brunch and have different events that rotate so check out the website prior to going! They’re a large restaurant with easy seating to accommodate bigger groups and provide the best party atmosphere for bach parties. It is 21+ but minors are allowed with a guardian before 7 pm on weekdays and before 1 pm on weekends.

Taylor's Tip

Quirky New American restaurant to grab a fun dinner & drink before a night out in Logan Square. Hyperlocal & delicious beer options and lots of really unique cocktail. I especially love the Goat Cheese & Ricotta Cappelletti! Grab an Uber or Lyft to head here and plan on staying here all night to make the most of your trip to the neighborhood!

Taylor's Tip

FREE and small but mighty zoo right next to the lake, surrounded by the skyscrapers of the city! They host special events frequently, like the Summer Wine Fest and Holiday ZooLights, so check if there’s anything extra fun going on before you go! I recommend driving, biking, public transit, or using ride share since it’s a bit north of downtown, unless you’re walking distance after brunch at The Vig!

Taylor's Tip

Especially great for fans of SNL, but either way, you’ll leave with a stomach ache from laughing so hard! Offer to be a part of the show when they ask for audience participation! It makes it so much funnier and memorable for you! This comedy club is where many famous comedians got their start, such as Steve Carrell, Tina Fey, John Belushi, Amy Poehler, Bill Murray, Cecily Strong, to name a few.

Taylor's Tip

Get there early to beat some of the crowds. Don’t miss the animal spotlight! You might see penguins or dolphins or whales in action with crazy views of Lake Michigan & the city skyline! Parking isn’t very convenient. Your best bet is to walk, ride a bike (Divvy is a bike rental service all around), public transit, or ride share.

Taylor's Tip

Beautiful & historic park for a breath of fresh air on your way to the Shedd Aquarium. Rent a Divvy bike to ride around and check out the gardens. Don’t miss the iconic Bean sculpture, it’s actually named Cloudgate, but who calls it that anyways?! If you’re visiting in the winter, check out the massive tree and try your hand at ice skating in the park!

Taylor's Tip

They frequently rotate exhibits, so be sure to check ahead of time what will be available during your visit. Driving is the best option for a family to get here, and the museum offers convenient on-site paid parking garage. Buy tickets on line in advance as this helps to avoid long lines during busy seasons!

Taylor's Tip

Lots of fun family-friendly activities year round, with a climbing wall, mini golf, play garden, and skating ribbon (option in the winter to ice-skate!) Great spot to pack a lunch, with a picnic grove to eat at and enjoy the lakefront & skyline! Located right next to Millenium Park, so be sure to walk through there as well!

Taylor's Tip

Get there early and enjoy the newly developed Gallagher Way with shops & activities right outside the stadium. For those traveling with young kids, be weary of choosing bleacher seats. Though it’s fun for kiddos to bring gloves & try to catch a homer, the weekend crowds in particular can get a bit rowdy out there. I recommend taking the red line, which drops you off right outside of the stadium and will be full of Cubs fans.

Taylor's Tip

Multiple different sails are offered, but the fireworks sail is not to be missed! I recommend this for kids over an architecture or other riverboat tour as it’s likely to be better suited for them! Grabbing dinner in River North beforehand is a great option & will be an easy walk to Navy Pier to catch a sail! They typically run rain or shine so be sure to dress for the weather. They do have a full bar on board!

Taylor's Tip

Check out the city from a glass box on the 103rd floor of the Willis Tower! Learn some history and facts about the city as part of your tour & then see all of it spread out beneath you once you’re on the SkyDeck! I think checking out the SkyDeck as part of your celebration will definitely help make it memorable! This is a once in a lifetime experience and you can plan special occasions with them! Book tickets in advance to guarantee your group & time will be accommodated

Taylor's Tip

Browse the Mag Mile for hours, checking out all of the shops and restaurants along the way. Nearly all of the top brands have spots along the mile, making this the perfect spot to treat yourself to a nice celebratory gift! Don’t forget to stop into Water Tower Place mall at the end of the mile for even more shopping & things to . For the coffee fiends like myself, the Starbucks Reserve Roastery and Ralph’s Coffee by Ralph Lauren are two must-stops!

Taylor's Tip

Now a nationally known beer, Goose Island originated in Chicago and has a fantastic brewery tour at their Clybourn Brewhouse, the longest continuously operating Chicago craft brewery. Brewery tours are limited to 12 people, so be sure to get tickets ahead of time for your desired date & time– also, they request that everyone wears long pants and close toed shoes for safety! Obviously, be sure to try a 312 before you leave! Paying homage to our gorgeous city, Goose Island’s most popular beer is named for the Chicago area code.

Taylor's Tip

Hanging out at the Playpen is the ultimate bachelor/bachelorette activity for groups that are looking to have a once-in-a-lifetime, luxury, unique party day! Charter a boat or luxury yacht for the day & hang out in the lake with plenty of other party people! The Playpen is a summertime hotspot where boats tie up and everyone drinks, floats, and parties all day.

Taylor's Tip

This is a bach weekend go-to because it is the neatest & most relaxing place to revive the group after a night out! It's located in a super cool repurposed warehouse, there’s multiple different baths for everyone’s preferences & options to add on different massage & spa treatments. Book in advance to be sure they’ll be able to accommodate your group!

Taylor's Tip

Love this option for bach parties that might be looking to save some money—the beaches are free to go to and you bring the party. North Ave Beach is the best spot for daytime partying– there’s beachfront bars & restaurants to keep you fueled all day. There are tons of sand volleyball courts and other recreation options there; book a court in advance or join a group when you get there!