8am: Grab breakfast at one of Chicago’s most iconic restaurants, Lou Mitchell’s
Is there a better way to start your day than with a Belgian malted pecan and bacon waffle at this iconic downtown cash-only diner that’s been slinging eats since 1923? No, there is not. That’s just science, people. View on Map
9am: Take a scenic boat ride, Vince Vaughn-style
As Vince Vaughn taught us in The Break-Up, there are many ways to see Chicago. But seeing Chicago by boat with a Chicago River and/or Lake Michigan cruise? You ain’t done Chicago ‘til you’ve done this, kid. Just resist the temptation to jump in the water, unless you’d like a free police escort to boat jail.
11am: Perfect your people-watching skills over lunch at Howells & Hood
Hours at sea makes a man (or woman) hungry and, while there are endless options in the Loop, it’s hard to beat the outdoor patio at Howells & Hood, located smack in the middle of downtown next to Tribune Tower. Anything is good, but the kimchi burger is the stuff of legend. View on Map
1:30pm: Walk the 606
It may not quite be NYC’s High Line, but the recently-opened 606 Trail is easily the coolest thing to open in Chicago in quite some time. Take full advantage of the four months of the year when the weather isn’t soul-sucking by exploring this 2.7-mile outdoor recreation path traversing through several hoods from Bucktown to Humboldt Park.
Noon: Pretend to work at Bridgeport Coffee
This all-day hangout helps anchor a recent neighborhood revival thanks to its welcoming, sunny vibe paired with standout roasts and four rooms of free Wi-Fi. In other words, it’s the perfect place to hole up for hours and (pretend to) get tons of work done. View on Map
1pm: Hang with grizzled old timers at Chicago’s oldest bar, Schaller’s Pump
Maria’s Packaged Goods is a worthy neighborhood institution, but when push comes to shove there are fewer places more uniquely Bridgeport than Chicago’s oldest continually running tavern which has been serving drinks (sometimes illicitly) since 1881. Besides a history lesson, grab a great parking spot and walk 15 minutes to The Cell for a Sox game. View on Map
2pm: Grab some of the finest baseball food in the world
With the two best teams in the game, baseball is king in Chicago. And while the Cubs hog the lion’s share of the glory, the Sox keep making the South Side proud along with some of the finest stadium food on the planet. Batting helmets full of barbacoa-topped nachos? Yes, please.
3pm: Hit one of Chicago’s best beach bars at the Waterfont Café
Instead of slamming beers with meatheads at North Avenue Beach’s famous Castaway’s, head a bit further north to discover a lakeside oasis of relaxation at this super-chill waterfront café, where you can listen to the ripples of the water as you order up your second (or third) lobster roll. View on Map
4pm: Commence maximum beach relaxation at Foster Avenue Beach
As you probably could have guessed by the above entry, the best beaches are found up north. And with wide open spaces and plenty of room for unfurling the blanket while opening a book in peace, Foster Avenue Beach is the best of the best.
7pm: Catch underrated underground comedy at pH Theatre
Not only is Edgewater one of Chicago’s most underrated hoods, it also houses one of its most underrated comedy theatres. While no one would fault you for going to Second City, you won’t be awkwardly sandwiched into a table next to a couple from Iowa at this locals-heavy temple of DIY upcoming improv talent. View on Map
5pm: Navigate the underground pedway
Save the architecture tour and trip to the Willis Tower skydeck for when your parents are in town. Real Chicagoans walk the underground pedway, a mysterious and maze like system of underground tunnels that will have you beating the traffic… as long as you know where the hell you’re going.
7pm: Party on a sexy hotel rooftop at Vertigo Sky Lounge
Do you like DJs and fire pits? Then you’ll love Vertigo Sky Lounge, Chicago’s only year-round indoor/outdoor lounge where the beautiful people go to be seen while sipping cocktails and enjoying panoramic city views 26 floors up at the Dana Hotel. View on Map
7pm: Watch MLB’s number one team demolish the competition at a Cubs game
Obvious choice? Maybe. But there’s a reason you braved the crowds -- to catch a game at one of the world’s finest ballparks. It also the helps that the Cubs are the best team in baseball. Oh yes, this is the year. Believe it.
10pm: Drink the only certified organic beer in Illinois at Uncommon Ground
As one of the “greenest restaurants in the country,” Uncommon Ground is famous for its organic rooftop farm that grows herbs and produce that are used at both its Wrigleyville and Edgewater locations. It also recently opened the state’s first certified organic brewery, Greenstar Brewing. View on Map
6pm: Explore one of Chicago’s finest art scenes on foot
Not only is Pilsen overrun with some of coolest and most colorful murals in the country, it is also a burgeoning arts center that you can explore by foot whenever the hell you want. Or, if you’re into organization, stop by on the first Friday of the month to tour open studios and galleries around the hood.
11pm: Turtle racing at Big Joe’s
Local dive bar Big Joe’s hosts turtle racing every Friday night as your antidote to the ordinary. Get a raffle ticket to be assigned a turtle, who will then “race” other shell-bearing reptiles across an 8-foot wide track that resembles a cross between a curling rink and ice hockey table. Just remember, there are rules. View on Map
9pm: Get dinner on one of Chicago’s finest patios, Big Star
Tacos on the patio at Big Star are a right of passage in Chicago. And if you show up at night instead of crowded sunny day you might actually get a table, as they’re slinging tacos al pastor and mescal shooters on the patio ‘til 2 or 3am. View on Map
10pm: Visit a speakeasy above a taco shop at Bordel
Yes, you could just walk across the street from Big Star to Violet Room, one of America’s best cocktail bars/speakeasies. But if you’re in the mood for something different, why not visit a different speakeasy… this one above Black Bull. It’s called Bordel and it slips under the radar with burlesque shows, flamenco dancers, and obligatory sexy red velvet. View on Map
More From Social Club
Drink up and feel a little less guilty about it at the first organic brewery to open up in the area.
Maria's is an awesome dive bar with eclectic selections and friendly staff.
1. Big Star1531 N Damen Ave, Chicago
2. Bordel1721 W Division St, Chicago
3. Black Bull Tapas1721 W Division St, Chicago
4. Happy Village1059 N Wolcott Ave, Chicago
5. The Boiler Room2210 N California, Chicago
6. 90 Miles Cuban Cafe2540 W Armitage Ave, Chicago
7. East Room2828 W Medill Ave, Chicago
8. Punch House1227 W 18th St, Chicago
9. Dusek's1227 W 18th St, Chicago
10. Thalia Hall1807 S Allport St, Chicago
11. Rossi's Liquors412 N State St, Chicago
12. Vertigo Sky Lounge2 W Erie St, Chicago
13. The Dana Hotel660 N State, Chicago
14. Lou Mitchell's565 W Jackson Blvd, Chicago
15. The Gingerman Tavern3740 N Clark St, Chicago
16. Uncommon Ground1401 W Devon Ave, Chicago
17. Greenstar Brewing3800 North Clark Street, Chicago
18. Waterfront Café6219 N Sheridan Rd, Chicago
19. Castaways Bar & Grill1603 N Lake Shore Dr, Chicago
20. Hopleaf5148 N Clark St, Chicago
21. Hamburger Mary's5400 N Clark St, Chicago
22. Big Joe's1818 W Foster Ave, Chicago
23. Bridgeport Coffee Company3101 S Morgan St, Chicago
24. Schaller's Pump3714 S Halsted St, Chicago
25. Maria's Packaged Goods & Community Bar960 W 31st St, Chicago
26. Skydeck Chicago233 S Wacker Dr, Chicago
27. Howells & Hood435 N Michigan Ave, Chicago
28. The pH Comedy Theater1515 W Berwyn Ave, Chicago
29. Parson's Chicken & Fish2952 W Armitage Ave, Chicago
30. Archery Bow Range Chicago1757 N Kimball Ave, Chicago