City Guides

Chicago City Guide

Lollapalooza is finally here and if you’re flocking to Chicago to see Mumford & Sons and The Cure, here are the best places to stay and play!

PACKING LIST Comfortable shoes? Check. Cut-off denim shorts? Check. Breezy T? Check. If you have your Lollapalooza style squared away, don’t forget to throw these essentials into your bag too:

  • Chapstick with SPF
  • Cross Body Bag
  • Straw fedora or hat
  • Sunglasses
  • Sunscreen
  • Towel or blanket – Pack even lighter with a scarf to sit on during the day and wear over your shoulders come nightfall.
  • Water bottle – Lollapalooza security requires sealed bottles of water so leave your Nalgene at the hotel.


TIPS Download the free Lollapalooza app to your smart phone to help navigate the vast Grant Park grounds and plan your own Lollapalooza schedule so you can be sure to see all your favorite bands.

Wear your bathing suit under your clothes. The wicking fabric will keep you more comfortable than cotton. Bonus: the summer temps may lead you to take advantage of any body of water nearby and you want to be prepared!

DINE A day of dancing, singing, and swaying can really build up an appetite. Here’s a list of our must-try Chicago dining institutions and newcomers.

Lou Malnati's Pizzeria A trip to Chicago wouldn’t be complete without trying the city’s world famous deep-dish pizza. Head over to this acclaimed local favorite that has been around since 1971, when Lou opened his first namesake restaurant and cemented the Malnati name as a pioneer in Chicago pizza.

Mercat a la Planxa If you’re looking for a culinary hotspot near Grant Park, then this Spanish tapas restaurant will certainly fit the bill. Chef Jose Garces, winner of The Food Network’s The Next Iron Chef, takes you on a tour of Barcelona with Catalán cuisine. We recommend ordering the sangria flight and sample each flavor!

The Bongo Room Before heading to Lollapalooza for a packed day of singing and dancing, fuel up at brunch spot The Bongo Room. Indulge in their sweet breakfast options, like the Red Velvet Hotcakes, or swing by for a savory lunch, like the Beef Tenderloin Sandwich.

Zed 451 Located in downtown Chicago, Zed 451 is a stylish restaurant with a delectable and unique dining experience. At their Harvest Tables, the chefs offer unlimited sampling of their meats, seafood, soups, salads, cheeses, breads, and charcuterie. On Sundays, enjoy the same experience with your favorite brunch dishes.

DRINK When you want to host your own Lollapalooza after party, head over to these Chicago hotspots for a post-concert cocktail.

Terrace at The Trump Sip on a craft cocktail while taking in one of Chicago’s most stunning views. Located on the 16th floor of the Trump International Hotel and Tower, The Terrace sits above the river and provides panoramic views spanning from the Willis Tower (formerly Sears Tower) to the John Hancock building.

Kasey's Tavern This neighborhood bar is the perfect place to unwind after a long day at Lollapalooza. Just a short walk from Grant Park, enjoy friendly company over a good beer at reasonable prices. The only downside is you’ll have a tough time choosing from their rotating menu of over 40 beers!

Sable Kitchen & Bar Behind one of the city’s biggest bars (literally speaking, the bar is 40 feet long!) is head bartender, Mike Ryan, known for experimenting with his extensive cocktail menu. Order one of his new Spanish-inspired gin and tonics, topped off with unique garnishes like pineapple or rosemary, or any classic cocktail you could desire. Nibble on some fantastic snacks too, like veal meatballs, from acclaimed chef Heather Terhune.

DO If you’re in town longer than the Lollaplooza weekend, enjoy these Chicago draws and highlights.

Oak Street Beach Unlike most cities, Chicago has 26 miles of untouched shoreline and 33 beaches – perfect to escape the urban jungle and summer heat. Oak Street Beach is a haven for Chicago’s chicest set. Flaunt your new swimsuit to swim in the deep waters, play volleyball, or relax under the blazing sun.

Fashion and the Field Museum Collection: Maria Pinto Hurry to catch this exclusive exhibit before it closes on August 18th. Esteemed Chicago fashion designer Maria Pinto curated this showcase of avant-garde clothing from the Museum’s collections and her own contemporary pieces. You’ll find a crocodile skin vest alongside Pinto’s exclusive collection for this exhibition, inspired by 19th century Chinese theatrical headdress.

Skydeck Looking for a truly unique Chicago experience? Climb up to the 103rd floor of the Willis Tower, the tallest building in the western hemisphere, and step out onto The Ledge – a suspended glass box that is 1,353 feet in the air at the Skydeck observatory. We dare you to look down!