chicago
Day One: River North, Lake Front, Mag Mile, and Crime Tour
- From Columbus, we have a direct flight, leave at 7:30am, arrive at 7:30am with the time zone change. Take the Orange line into the city (about 20 mins).
- 8:15AM. Check bags at River North hotel. Lots of places to stay, we have airbnbed near Lincoln Park before.
- 8:30-9:15AM. Egg Harbor Cafe (220 E Illinois St). San Antonio Skillet, a tex mex dish, wonderful.
- 9:30-12:30PM. Chicago's Ultimate City Bike Tour. (540 N Lake Shore Dr). This is one of many tours offered by Bobby's Bike Hike Chicago. This one focuses on downtown, must see Chicago sites. Longer tours featuring more neighborhoods and mixing in food/beer are available.
- 12:30-1:00PM. Relish Chicago Hot Dogs (550 E Grand) near Navy Pier if first stop. Classic Chicago Dog, lemonade, and Italian ice. Great snack/lunch.
- 1:00PM-2:00PM. Navy Pier (600 E Grand). You can spend a lot of time here, rides and food. I liked just walking around a famous Chicago landmark and checking out art & statues.
- 2:00-4:00PM. Magnificent Mile shopping. High end stores like Saks Fifth Ave and Nieman Marcus to affordable stores like Marshalls. IT'SUGAR is a fun candy store, lots of 70's classics. If shopping is your thing, you could spend all day here. See the famous Chicago Water Tower and the Cow Parade.
- 4:00-6:00PM. Chicago Crime and Mob Bus Tour (163 E Pearson St). Sights and stories of the famous criminal history of Chicago, see more below.
- Option for this day: Bikes, Bites & Brews®- Chicago’s Signature Dishes Bike Tour (540 N Lake Shore Dr),,,,,, 4 hour tour, another great way to see the city and sample the foods.
- Option for this day: Field Museum, Shedd Aquarium
- 6:15-7:15PM. Bar Stool River North (14 W Hubbard). Okay, we were way too old for this crowd and the loud pumping music, but wanted to check it out b/c Bar Stool college football coverage on social media is entertaining.
- 7:15-8:15PM. II Porcelino (59 W Hubbard). Nice place, good Italian, upscale with reasonable prices. Chicken Piccata and Brussel Sprouts were highlights for me. Big bonus, they had Off Color Brewing Apex Predator, a tasty farmhouse ale.
- 8:30PM+. Howl at the Moon (26 W Hubbard). Yes, breaking the rules of avoiding chains, but this place was fun, we enjoy the piano bars (Pat O'Briens in New Orleans is fun as well). Good news, they had Daisy Cutter from Half Acre.
Day two: Lincoln park, lakeview, wrigley, laughs
- 8:00-9:00AM. Wishbone (161 N Jefferson St). New Orleans themed breakfast. It's all good, but recommend the cajun omelette or chicken andouille hash to experience the unique dishes.
- 9:00 - 9:30AM. Take the Brown line North at Merchandise Mart and get off at Armitage. NOTE: Lori's Shoes (824 W Armitage) is at this train stop, one of Kristi Jump's favorites.
- 9:30AM-11:00AM. Walk through Oz Park (see below) and go to Lincoln Park Zoo (free).
- 11:00AM-12:30PM. Walk up Clark with a detour down Broadway through Lakeview on way to Wrigleyville. Consignement and discount shopping paradise. Recommendations in order Crossroads Trading (2711 N Clark), Banana Republic Outlet (2720 N Clark), TJ Maxx (2739 N Clark), The Xchange (2907 N Broadway), Elliott Consignment (3015 N Broadway), Out of the Closet (3311 N Halstead), Beatnix (3400 N Halstead).
- Option: Obviouly, you can spend more time at zoo or shopping, it's your prerogative, but don't short cut pre-game for Cubs. Tip: you can store bags at wrigley for only about $6 at usebounce.com.
- 12:30-2:00PM. Pre-Game for Cubs. Sluggers World Class (3520 N Clark) has batting cages on the 2nd floor, Cubby Bear (1059 W Addison) and Murphy's Bleachers (3655 N Shieffield Ave) are classics.
- 2:05-4:30PM. Cubs day game.
- Option: Stay in Wrigleyville. Food/Fun recommendations: Old Crow Smokehouse (3506 N Clark) is a large place with great food, Browns and Buckeyes backer bar. Happy Camper (3458 N Clark) is thin crust pizza in a Camper, it has a 70's vibe.
- 5:00-5:45PM. Dryhop Brewers (3155 N Broadway). Good place for a flight with a wide variety of beers, liked the American IPA, Wizard Night, the best.
- 5:45-6:45PM. Wilde Bar and Grill (3130 N Broadway). Nice place with large selection for all tastes and budgets. Upscale but not overpriced and snooty. Maybe the best brussel sprouts ever. I like the Rueben but others go for the Ultimate Grilled Cheese with Bacon
- 7:00PM+. Laugh Factory (3175 N Broadway). Been here a few times, they have several comedians perform, with little time, you get their best jokes.
Day Three: NW MIlwaukee Ave Neighborhoods and Art Tour
- 9:00-10:00AM. Bongo Room (1470 Milwaukee Ave). This is in Wicker Park, need to take the Blue line which runs parallel with Milwaukee Ave. Spicy Turkey Sausage Burrito comes with tomatillo salsa,
- 10:00-12:30PM. Consignments again. Buffalo Exchange (1478 N Milwaukee), Ragstock (1459 N Milwaukee), Vintage Underground (1507 N Milwaukee), Crossroads Trading (1519 N Milwaukee).
- 1:00-3:15PM. Offbeat Street Art Tour of Chicago. (1649 N Damon). Fantastic tour, great way to walk the neighborhoods. See more below.
- 3:30-4:30PM. Pilot Project Brewing (2140 N Milwaukee). Flights from home brewers, pretty cool.
- 5:00-6:30PM. Revolution Brewing (2323 N Milwaukee). Good beer and food in fun atmosphere. Very large beer menu that you will not find in the store, many IPA's to try.
- 7:00PM+. Back to RiverNorth, that's about it, maybe get a beer in the bar at Harry Carey's (33 W Kedzie).
More tips for chicago visit
- More Suggestions, maybe take several 3dayvacations: You can spend a full day at the Museums and the Aquarium. We went to a local October Festival near Lincoln Park one time, lots of fun. Chicago is fun just to experience neighborhoods, food, and drink.
- Old town is another place to go. Second City comedy club with a really cool rooftop bar, Utopian Tailgate. Across the street is the famous comedian hang out, Old Town Ale House.
Details & Descriptions
CHicago Crime Mob Bus Tour
Offbeat Street Art Tour of chicago
CHicago Crime Mob Bus Tour
Chicago Crime and Mob Bus Tour is a great way to see the city and learn about the beer wars, Capone, Dillinger, Elliot Ness, the St Valentines Day Massacre, etc.
Bobby's BIke Hike
Offbeat Street Art Tour of chicago
CHicago Crime Mob Bus Tour
Bobby's Bike Hike (540 N Lake Shore Dr) has tours and bike rentals, whether a tour or just renting bikes, Chicago's Lakefront Trail offers car free biking to Millennium Park (the bean), Buckingham Fountain (Married with Children), Chicago Riverwalk, Navy Pier, Lincoln Park Zoo, and Wrigley Field.
Offbeat Street Art Tour of chicago
Offbeat Street Art Tour of chicago
Offbeat Street Art Tour of chicago
Offbeat Street Art Tour of Chicago is our favorite, even if you are not into Street Art, this is a great tour with many famous faces. The Robin WIlliams commissioned for suicide prevention week is heart breaking. Other highlights include John Lennon with Imagine Lyrics and works by Hebru Brantley. Also, great way to see the neighborhoods of west Chicago.
Offbeat Street Art Tour of chicago
Offbeat Street Art Tour of chicago
Offbeat Street Art Tour of chicago
Offbeat Street Art Tour of Chicago is extra picture of a Hebru Brantley
Cubs Game
Offbeat Street Art Tour of chicago
Laugh Factory
Laugh Factory
Offbeat Street Art Tour of chicago
Laugh Factory
Acme Feed and Seed has good food at reasonable prices in a fun atmosphere, cleaner and not as loud as other places on Broadway. We ate on the Rooftop with a view of the Cumberland River