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Chicago Itinerary

How long was your stay?

3 Days

How did you travel?

With Friends

Tell us why you traveled to this destination.

Traveled there for a wedding and visited a friend who lives there as well.

What was your itinerary?

Day 1: Explored Millennium Square, had lunch at Giordano’s
Day 2: Went to Navy Pier, Chicago Zoo
Day 3: Visited Wrigleyville

Give us all the details! Tell us where you went and what you did on your trip.

Day 1: My friend lived right in the heart of town, so we were a quick walk or metro to anything we wanted to do. I was there in the wintertime, so the first thing we did was head to Millennium Square to see the famous bean! I actually love the Bean, for pretty much no reason, but it’s fun to go get your touristy pictures and the park it is nestled into is huge with a ton to do, especially in the winter. They host all kinds of events there, and in the winter there is an ice rink. We decided to go ice skating, and it was so much fun.

After that, we walked the main strip from Millennium towards the river and grabbed lunch at a traditional Chicagoan deep-dish pizza place called Giordano’s. It’s one of Chicago’s most popular. For sunset, we had reserved ourselves a time slot at the “Top of the Rock”, basically Chicago’s version of the Empire State, except you can walk onto the glass out from the building a few feet. Spooky! Make sure you get those reservations in advance as well, as it sells out, and even when you have a reserved time the line is long. There is of course a bar at the top as well. In the evening, we went to an Irish pub in Lincoln Park called River Shannon which is known for being extremely dog friendly, so everyone brings their dogs! It’s a fun little spot to cap the night.

Day 2: In the morning, we rode electric city bikes over to the Navy Pier that stretches into Lake Michigan. Basically, it has an indoor mall and food court with multiple mini-breweries along the way as well as a small amusement park. It’s fairly big, and you can also take a lot of boat tours from there. It’s s fun spot to hit to just stroll, eat good food, get drinks, and be out near the water. We got coffee and a late breakfast there and sat outside. Once done there, we headed over to the Chicago Zoo. There are 2 you can choose from – Lincoln Park and the Chicago Zoological Park. The Chicago Zoo is free! And big, with a ton of animals. We opted to go there and had a blast. We spent the entire back half of our day there before heading to dinner nearby.

Day 3: On our last day, we left a lot of time for us to mill around and have a more laid-back day. There are tons of Parks in Chicago as well as beaches for the summertime fit with bars and cabanas. We wanted to go check out Wrigleyville even though baseball was out of season, so we grabbed city bikes again and rode along the bike path along the lake to get there. You can still go to the stadium and the surrounding area to explore. It’s a very popular, and young area of Chicago with very unique bars and restaurants, as well as museums paying homage to Wrigley and the Cubs. We took a little tour of the stadium, found some fun bars, and ended up spending the majority of our day there. Another option for a laid-back day would be to walk the river, with countless rooftops and outdoor bars and places to eat where you can socialize and have a great day out near the water.

Would you recommend this trip to a friend?


What was the highlight of your trip?

The bean!
Ice skating
The Zoo

If you were to take this trip again, is there anything you would add or do differently?

Make sure you dress for the season! Chicago gets COLD, and it gets HOT.
Some metro lines are a little less safe than others. Generally, the Red Line is seen as the least safe, and gets “worse” the more south that you go.

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