The city skyline as seen from Promontory Point on Chicago’s South side.
For now, direct flights between ORD and MRY are on Saturdays only. That gives you a week. As a former Monterey County resident transplanted to Chicago, here’s my recommended itinerary:
SATURDAY EVENING: Fly into O’Hare around 8:40pm. Hungry from the flight? Look no further than Tortas Frontera (Terminals 1, 3 and 5; United Airlines flies into Terminals 1 and 2), which made the New York Times’ latest “25Best Restaurants in Chicago Right Now” list. Hail a ride. Check in and settle into lodging.
SUNDAY DAY: Take an architecture boat tour; if you have time, do one that takes you out onto Lake Michigan. This is something locals like to do on occasion.
A lovely day on the Chicago River as seen from the Michigan Avenue bridge.
SUNDAY EVENING: Take the Blue Line to Logan Square to have dinner at Reno Chicago or Lula Café, and afterward get a nightcap at the craft cocktail bar Billy Sunday.
MONDAY DAY: Go to the Art Institute of Chicago, regularly voted one of the best art museums in the world.
The writer takes a selfie next to one of the lions flanking an entrance to the Art Institute of Chicago.
MONDAY EVENING: Check out Zanies (Old Town) or the Lincoln Lodge (Bucktown) to see live, local stand-up comedy; if you go to Zanies, stop for dinner at Twin Anchors for the ribs.
TUESDAY DAY: Visit the (free) Lincoln Park Zoo, but first stop at nearby Beacon Donuts, which is hidden in the alley and slings the best – and all-vegan – donuts in the city.
TUESDAY EVENING: Get tickets to the Chicago Crime Tour, a bus tour that begins and ends on the Magnificent Mile (Streeterville) and stops at historic crime spots (the evening tour also includes a slice of traditional Chicago-style deep-dish pizza).
WEDNESDAY DAY: Walk around “The Loop” to find public art by Picasso, Chagall and Miro, and get coffee at Happy Monday, which is also in the Loop.
Cloud Gate, aka “the bean,” reflects the scene in Millennium Park.
WEDNESDAY EVENING: Go to The Green Mill jazz bar (cash only) in Uptown to see Alphonso Ponticelli & Swing Gitan play gypsy swing jazz from 8pm-midnight. The Green Mill is also a solid option on Fridays for happy hour with Chris Foreman, the blind singer who plays the organ behind the bar and on Saturdays at 3pm for the standing-room-only Paper Machete variety show featuring local musicians, comedians and actors alternating their acts between the main stage and the stage behind the bar.
THURSDAY DAY: Visit the Field Museum (Museum Campus) to see dioramas and an extensive collection of dinosaur skeletons and fossils including Sue, the most complete Tyrannosaurus Rex specimen in the world.
THURSDAY EVENING: Go to The Wiener Circle for a traditional Chicago-style hot dog (beware when ordering the $20 chocolate shake… if you know, you know) and then head to iO Theatre for an improv show.
Tiffany Dome at the Chicago Cultural Center.
FRIDAY DAY: Spend a day at Montrose Beach on Lake Michigan (one of Chicago’s legal surf spots).
FRIDAY EVENING: If you can get a reservation, go to Kumiko for either the tasting menu or for the basement whiskey bar, regularly voted one of the best bars and bar programs in the world.
SATURDAY MORNING: Cry tears of joy because you just fell in love with Chicago and your flight leaves at 8:40am. You should be back in Monterey by lunch time.
(0) comments
Welcome to the discussion.
Log In
Keep it Clean. Please avoid obscene, vulgar, lewd, racist or sexually-oriented language.
PLEASE TURN OFF YOUR CAPS LOCK.
Don't Threaten. Threats of harming another person will not be tolerated.
Be Truthful. Don't knowingly lie about anyone or anything.
Be Nice. No racism, sexism or any sort of -ism that is degrading to another person.
Be Proactive. Use the 'Report' link on each comment to let us know of abusive posts.
Share with Us. We'd love to hear eyewitness accounts, the history behind an article.