A great outdoor patio is worth celebrating. But if you really want to eat outside in Chicago, your best bet is to pick up your own food and set down a blanket in one of the city's amazing parks.
Below are a few of our favorite food pitstops by Chicago's parks, which should help you stock up for the best impromptu picnic possible.
This oasis in the Loop is set up for maximum picnic-ability, with glorious green spaces, long rows of benches, and dozens of tables. A few years ago you'd have to make due with a poorly made sub, but now there are now some incredible options nearby. The first is Toni Patisserie and Cafe, a charming French-inspired shop with elegant and simple sandwiches served on crispy bread. Plus, it's located all of a half a block away. Pastoral, which is a block north, has equally delicious sandwiches, and also has a plethora of charcuterie and cheeses—if you'd like to go that route.
Though chugging a brown-papered-bag of beer by the Bean is against the law, you can legally drink beer and wine at the Jay Pritzker Pavilion and the Great Lawn during most free events. Completing its status as a one stop for all you picnic needs, Pastoral has all the wine you'd need. Of course, if you just need something quick and cheap, the flagship Walgreens on State Street is close. Fulfilling its corporate goal of being the "most innovative, forward-thinking" Walgreens out there, it has a conveyor belt of booze that is worth checking out. Oh, and it also sells sushi.
For most of the northern half of Grant Park, the same options as Millennium Park apply, but the park also stretches south another mile. On its southern edge, it's hard to go wrong with Panozzo's Italian Market. Featuring a collection of antipasti and a good collection of sandwiches and salads, it's a good all-around stop.
Lincoln Park, Southern End
On Wednesdays and Saturdays, there is no better option than the Green City Market, which is located near the southwest corner. The outdoor market features a collection of quirky food stalls (including some really awesome tamales) along with cheesemongers, numerous bakers, and some amazing fresh fruit (and any vegetables you'd need later on). For the rest of the week, nearby Treasure Island offers a respectable collection of the basics. Oh, and though you are technically not having a picnic, Perennial Virant's outdoor patio is the next best thing.
Lincoln Park, Northern End
Another Pastoral outlet is located within walking distance of the northwest corner of N. Sheridan and Diversey, and is, once again, a great place to pick up bread and cheese. But the closest option is Red Hen Bread, where you can pick up a solid sandwich or salad.
Plans are on the way to revamp the most popular tourist attraction in Illinois, but for the time being at least, the food options are skippable. Still, the commanding skyline views are free, and a picnic is the best way to take them in without having to pay dearly. Luckily, all the picnic supplies you need are available at Fox & Obel, one of the better grocery stores in all of Chicago. Load up on bread, cheese, and charcuterie, or simply pick up one of the many prepared meals.
Chicago's food truck scene is hobbled by laws and regulations—except, that is, at Humboldt Park. There you can find a number trucks where people are actually allowed to cook on board. Most of them specialize in Puerto Rican favorites, including lechon (roast pork) and jibaritos. The most popular truck by far is La Esquina Del Sabor, which serves up huge portions of fatty pork. But there are loads of great options. Hot Bunz dishes out a solid natural casing hot dog, while Isla de Cafe serves up sandwiches from a silver airstream. (Note: Look up the truck before leaving, as some have strange schedules.) One of my favorites is La Bomba Place on the west side of the park, where I can pick up a meaty lechon sandwich plus a huge side of rice. Once I have my order, I like to walk up the small hill by the truck, stretch out on the grass, and take in one of the best views in all of Chicago.
I'd never even heard of Union Park until it was picked as the location for the yearly Pitchfork Music Festival, but thanks to influx of new residents in the area, it's turned into a nice green enclave in the middle of the industrial grit of the West Loop and the oceans of parking lots by the United Center. Of course, I could be hanging out there so often because it's close to La Lagartija and Bombon Cafe, two of my favorite Mexican restaurants in the city (which also happen to be owned by the same couple). Tacos don't travel especially well, but Bombon's tortas featuring house-made bread and the composed salads sure do.
Jackson Park and Promontory Point Park
Hyde Park has a collection of solid delis and cafes that are close to Jackson Park and, my personal favorite, Promontory Point Park. My current favorite is probably Zaleski & Horvath MarketCafe, a full service deli that serves some seriously good sandwiches. There are two locations, but the one on 57th is probably the closest option.
I wouldn't call these places close, but many of the best barbecue joints on the South Side (including Uncle John's, Lem's, and Barbara Ann's) don't have seats, and while eating on the truck of your car is a good choice, the best option is driving a few miles east to feast on rib tips and hot links in Jackson Park.
Forget the epic lines on the patio, this is the perfect time to take advantage of Big Star's to go window. Though I mentioned above the tacos don't travel well, they should be able to make the 15 foot trek across the street to the triangle shaped park. Sadly, you won't be able to carry that margarita.
Obviously, there are more parks. Technically, there is the entire lakeshore, which lines the eastern edge of the city, not to mention the dozens upon dozens of small parks around the city. Let me know what other places make for good quick stops by a park!