Long Weekend Guide to Chicago
Where to stay, what to see, what to eat, and how to get around on your long weekend in Chicago.
Imagine a city that is very tightly packed together making it very much a walkable city, lined by a lake that resembles an ocean, a mile long strip of “magnificent” shopping, enough room for a park, detailed buildings, a river that cuts through the city creating beautiful bridges with a river walk, and deep dish pizza all encompass the Windy City of Chicago.
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Where I Stayed
Chicago has plenty of nice sky rise hotels to choose from, but if you are looking for somewhere that stands out on its own that would be the Palmer House. Not only does this house scream elegance it could not have been in a more perfect location for everything we wanted to do this weekend. With this said we ended up being able to walk almost everywhere from the Palmer House. This hotel is now owned by Hilton, but has not lost any of its history or charm. Imagine being transported back in time and having a European feel to the inside architecture. Try not to run into any one as you gaze up at the painted ceiling. Make sure to spend some time in the lobby because it is that gorgeous. Grab a drink and sit on the balcony overlooking the ornate lobby. I can just imagine elegant balls and galas taking place in this room. No worries about waiting on an elevator. There are 12 golden ones accessible from the hotel lobby.
What to See
Architecture Boat Tour
Our first day here we introduced ourselves to the city with a boat tour along the Chicago River. This was the perfect introduction to the history behind Chicago, all the intricate detail and meaning behind each building (I was amazed at how many high rises where squished together in a pretty small area), beautiful views, and a nice way to get the lay of the land for the rest of our long weekend.
TIP: I used a tour found through Viator.
Magnificent Mile
A mile long road of shopping that they named magnificent! This bustling side of Chicago is lined with flag ship stores, upscale shops, cool restaurants, and hotels. Strolling along the mile you will spot the Water Tower, the Tribune Tower, the John Hancock Center, and the Wrigley Building. We came here everyday of our visit as it encompasses so many must spots (including my favorite EATALY that runs perpendicular to it).
Expect a line, but go up in the sky to the 100 story John Hancock Center to find panoramic city views in the Signature Room.
The Bean
The iconic bean! Around the Field Museum and Millennium Park congregate to the massive crowd around the Bean. I did not know that this was just a nickname and that the sculpture’s real name is Cloud Gate. (Thanks to the location feature in the Photo app on iPhone I have learned something new.) It is so neat how clear the reflection of the city and the sky shine off its stainless steal.
Millennium Park
After visiting the Bean we made our way over to Millennium Park. We happened to be there during Jazz Fest, but check in advance to see what artists will be here when you are.
201 E Randolph St, Chicago, IL 60602
Buckingham Fountain
Before heading over to walk Chicago’s Lake Front Trail, take in the magnitude of Buckingham Fountain!
301 S Columbus Dr, Chicago, IL 60605
Lake Front Trail
Continuing our walk towards Navy Pier we walked along Chicago’s Lake Front Trail. There is something about water that is so relaxing. The ocean like Lake Michigan is dotted all over with sail boats. It is so pretty to take a break and sit and gaze out into the never ending waters.
Navy Pier
Navy Pier is your ultimate 3,300 foot long pier. Experience a ferris wheel, pick from numerous restaurants, relax at the beer garden, or gaze out at Lake Michigan.
600 E Grand Ave, Chicago, IL 60611
Lincoln Park
This neighborhood reminded me so much of San Francisco with its Victorian homes. A little out from the city, but easily reached by the CTA train lines or Lyft, you can find some amazing, quieter views of the city.
2001 N Clark St, Chicago, IL 60614
Wrigleyville
Home to the historic Wrigley Field this part of town is lined with restaurants and bars full of excitement for baseball. Back home I have seen crowds like this for football, but never this magnitude for baseball.
1060 W Addison St, Chicago, IL 60613
Chicago River
How unique does this river make Chicago?! This river reminds me of the Grand Canal in Venice, almost. It also has its own trail to walk along as you walk through the city. The golden hour was my favorite time here as the sunset displays all its colors onto the buildings and water. Take in a relaxing start to your evening at City Winery along the river with one their wine selections.
1200 W Randolph St, Chicago, IL 60607
Chicago Theater
Extremely close to the Palmer House is the 1920’s landmark Chicago Theater located in the Loop district. If you are a music lover or enjoy plays make it a point to see who is in town when you are.
175 N State St, Chicago, IL 60601
Goose Island Brewery
If breweries are your thing make a stop at Goose Island. It is local to Chicago so expect to find very few tourists here. Their roots began in Lincoln Park where they named themselves after a near by island. They offer a variety for everyone to find a favorite.
1800 W Fulton Street Chicago IL
United Center
Sports fans must! Home to the Chicago Bulls and Chicago Blackhawks, this stadium houses the Michael Jordan statue for your die hard basketball fans.
Where to Eat
Lou Malnati’s Pizzaria
Go for the deep dish with the butter crust! TIP: We ordered the small for the 2 of us, and we could not finish it.
805 S. State Street Chicago, IL 60605
EATALY
Probably my favorite place on earth right now. I am not exaggerating as we did eat here 2 out of the 3 days we were here. All authentic Italian everything. In this indoor marketplace you can shop, drink, eat, and feed your sweet tooth. There are areas devoted to, gelato, coffees, crepes, vine, birra, pasta, cheese, pizza, seafood, and meats. No matter where you are you can have all of these. You are able to walk around with your beverage and no matter the restaurant you chose they can grab you anything you want that is from inside the building. It is right off the Magnificent Mile so do not miss this stop. TIP: Make sure to make a reservation at the specific restaurant you are wanting. (pasta, seafood, meats).
Check out this baby! Gelatto with homemade chocolate chip cookie and spaghetti!
Make sure to bring something home with you! I came home with some limoncello and birra from their onsite microbrewery.
43 East Ohio Street Chicago, IL 60611
Butcher and Burger
Amazing burgers! They are more upscale and customizable even down to how your burger is seasoned. While this is not right in the city it is in the neighborhood of Lincoln Park. Very cute neighborhood with Victorians that reminded me of San Francisco! They do not serve alcohol, but you can bring your own beverage to dinner with you!
1021 W Armitage Ave Chicago IL 60614
Lucky’s Sandwich Company
We visited Wrigleyville for a Cubs game since the Braves were in town! If you have read my San Francisco blog post you will notice the Braves were in San Fran the same time we were too! I promise we are not die hard fans. Just a coincidence. Voted one of Chicago’s Best their sandwich is not ordinary by any means. So much food that I would definitely recommend sharing with a friend.
3472 N Clark St Chicago IL 60657
Bavette’s Bar & Boeuf
This was Chandler’s pick as he had visited here once before on a business trip and knew this was a place he wanted to share with me for a date night. I agree this is a very romantic setting for you and your significant other. If you are looking for a nice meal this authentic Chicago Steakhouse is your place. You will walk in and be taken back in time. The restaurant has dim lighting, with a wood setting, and crystal chandeliers. Ask for their special steak rub they make in house. They have a basement that has a full bar if you choose to hang out rather than eat a meal. Reminds me a lot of a speakeasy.
218 W Kenzie St Chicago IL 60654
How to get around
We got around majority of the time by our own two feet. I love cities that are walkable probably because of my love for the European culture. It is nice to take in everything at your own pace and experience a destination like a local. Some of the places we visited like Lincoln Park, Goose Island, and Wrigleyville we either took an Uber or Lyft or their metro. The metro is right on time, same time frame as a car, and extremely clean. The metro was even cleaner than some of the cars we used.
