How To See The Best Of Chicago In 3 Days: The Ultimate Chicago Itinerary
Chicago is without a question the best city in the Midwest. This booming metropolitan city has so much culture and history behind it. Each and every part of town has it’s own unique story and vibe. From old Italian mobsters like Al Capone, to jazz & blues legends, to hilarious stand-up comedians, to current heroes like Oprah and Obama, Chicago has bred many legends who have changed the world. Chicago is definitely a city worth visiting which is why I’ve put together the ultimate Chicago itinerary for you. Keep scrolling and comment your suggestions below. 🙂
Where to stay:
The Langham Chicago is the absolute best hotel to stay in Chicago. This Forbes Five Star Luxury Hotel is located right on the river and has the best view of the river. We stayed on the 12th floor in a Langham Executive Club King Room (Suite 1203) and it was glorious. Everything was perfect from the lobby to the Club Lounge to the spacious rooms. Here are some photos from our stay below.
Brunch at Travelle (Langham Hotel)
Shop on Michigan Ave
Boat tour on the river
Coffee at Hero Coffee
The Bean & Millennium Park
Drinks & dinner at The Allis (SoHo House Chicago)
Brunch at 3 Arts Club Cafe
Wrigley Field Park
Lunch at Dimo’s Pizza
Chicago Theatre Show
Dinner and rooftop drinks at the Ace Hotel Chicago
Brunch at The Chicago Diner
Go to a few of the many museums, art galleries, or exhibitions Chicago has. I found a list that has all the good ones included which you can see by clicking here. My suggestions are the Art Institute of Chicago which was named “#1 Best Museum In The World” by TripAdvisor, and also the Field Museum which has the largest dinosaur skeleton of a T-Rex on display.
Second City Comedy Club
Dinner at Lou Malnati’s
Drinks at Green Mill Jazz Club
Additional Suggestions & Tips
- If you go to Chicago in the spring or summer time, a Segway tour might be fun even though it seems super touristy! It’s another great way to see the city besides the boat tour:)
- Cindy’s Rooftop, RM Champagne, Watershed, Dine Machine, Joy District, Holiday Club, Wheat’s End Cafe.
- Kayak along the river, watch movies in the park during summer, shop in Gold Coast area & also Wicker Park, North Avenue Beach, Lincoln Park Zoo, The Adler Planetarium, The Shedd Aquarium, Broadway shows, opera shows, and the Gene Siskel Film Center.
For my NYC Weekend Itinerary, you can click here.
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