I’ve been looking through some of my old trips, and found that I had pretty good documentation on my itinerary for our trip to Chicago a couple of years ago! We went for a quick weekend away for a friend’s wedding.
I had never been to Chicago, and totally fell in love – I can’t wait to go back and eat even more food! The pizza, the cake shakes, the cocktails… But for now, this itinerary will have to do.
This was one of the first times we did more of a “menu” than a strict itinerary. We gave ourselves blocks of time where we could do several different things, depending on our mood. I’ll note some of what we ended up doing, but leave the other options in case you want to choose your own adventure!
Day 1
2pm – Flight lands in Chicago
Yay! We made it! Head to the city via the CTA Blue Line.
Follow signs for CTA Trains. Purchase Ventra Single-Ride Tickets for $3.50 per person. Follow signs for Forest Park Blue Line and swipe card as you go through turnstiles. For more detailed information, see this deep dive on How to Get from O’Hare Airport to Downtown Chicago.
3pm – Check-in at Langham Hotel
We stayed at The Langham Hotel, located just North of Washington Station. Checkin, unpack, change, and get ready for your first Chicago adventure! If you’re traveling in December like we did, you’re going to need to layer up!
4pm – Chicago Adventure
This first evening is prime time to go out an experience something. You’ve been traveling all day so you’re either exhausted or running on adrenaline and ready to go! Here are the options we considered in this time block:
- Christmas Market
- Holiday Afternoon Tea at Langham Hotel Pavillon (available until 5pm, $80/person)
- Visit 365 Observation Deck
- Visit Willis Tower Sky Deck
We ended up going with the Christmas market, which was very cold, but also really fun! We ate latkes, drank hot chocolate, and bought some Christmas ornaments (great travel souvenirs)!
7pm – Dinner
Dinner at Langham Hotel Restaurant: Travelle
Day 2
9am – Breakfast
- Wildberry Pancakes and Cafe (near Art Institute)
- The Gage (near Art Institute)
- Beatrix River North (North of Langham Hotel)
- Hotel Room Service
10:30am – Art Institute of Chicago
The Art Institute is a 15 minute walk from The Langham Hotel. On the way you will pass Millennium Park, Chicago’s famous sculpture park.
- Address: 111 S Michigan Ave, Chicago, IL 60603
- Saturday Hours: 10:30am – 5pm
- Website: https://www.artic.edu/
1pm – Pizza for Lunch
- Pizza at Prudential Plaza/Millenium Park Giordano’s (130 E Randolph St)
- Pizza at Downtown/ Central Loop Giordano’s (223 W Jackson Blvd)
- Pizza at The Art of Pizza (20min uber north of Langham Hotel)
We ended up getting pizza at a different Giordano’s due to crowds, but even if there are crowds when you go, it is very, very worth it. This is still the best pizza I’ve ever had in my life. Deep dish is now my thing.
2pm – Quick Chicago Adventure
- Visit Willis Tower Sky Deck
- Christmas Market
- Back to hotel early for mid afternoon break; we took a break and then prepped for the wedding!
5pm – Wedding Adventure
We spent this evening enjoying our friend Michele’s beautiful wedding. Since I can’t recommend that as your Saturday activity, I will encourage a fancy dinner somewhere posh! That’s pretty much what we did by attending the wedding, and it was a blast.
10pm – Post Wedding Cocktails/snacks
- My cousin recommended The Violet Hour, saying they make “the best cocktails in the city”
- Portillo’s is open until 1am. Hot dog. Cake Shake (100 W Ontario St, Chicago, IL 60654)
- Be super lazy and get Portillo’s Cake Shakes delivered to your hotel via Door Dash (yup, that’s what we did)
Day 3
9am – Breakfast
I’m honestly not sure what we did for breakfast… but I have this beautiful picture of pancakes, so I’m assuming room service?
- Langham Hotel Restaurant: Travelle
- Beatrix River North (North of Langham Hotel)
- Hotel Room Service
10am – 365 Observation Deck + Magnificent Mile
We checked out of our hotel, left our bags with bellhop, and then tried to arrive at the 365 Observation Deck on the earlier side. It was a great view, plus we got to see more of the lake, which we hadn’t seen much of at this point. Then we walked back to our hotel via the Magnificent Mile, windowing shopping a bit with the holiday displays.
2:45pm – Depart for Airport
From the hotel, walk six blocks to Washington Station. Purchase Ventra Single-Ride Tickets for $3.50 per person. Follow signs for O’Hare Blue Line and swipe card as you go through turnstiles. For more detailed information, see this deep dive on How to Get from O’Hare Airport to Downtown Chicago.
3:45pm – Arrive at Airport and Fly Home
**Featured image by Ricardo Esquivel
Leave a Reply