Chicago Weekend Guide

Chicago is the perfect city for a weekend getaway in the summer. The weather was perfect for site seeing and the city had so much to offer. I had a blast staying downtown and seeing the sights while indulging in deep dish pizza. Here are my recommended stops for resturants and things to do.

Copy this google map to use for your own vacation and make edits to see your top spots.

Restaurants & Bars

1.  Au Cheval

This burger bar is a must on your list of places to eat. If your traveling with a small group, save time an eat at the bar. The wait is usually over an hour. The wait time a testament to the quality of the burgers!

2. Lou Malnati’s Pizzeria

Chicago is known for their deep dish pizzas. Try Lou Malnati’s, they have multiple locations in Chicago.

TIP: The wait can be around an hour, but you can place your order for pizza as soon as you’re on the waitlist.

3. Giordano’s

Another great deep dish restaurant!

4. Wildberry Pancakes & Cafe

I really wanted to go here for brunch, but the wait was too long.

TIP: You can get on the wait list via yelp even before you get there.

5. Farmhouse Chicago 

Great brunch food! I loved everything on the menu.

6. Spiaggia

If you’re looking to splurge for dinner, make a reservation at Spiaggia.

7. Cindy’s 

Cindy’s is a great place to get a drink with a view of the city. It’s on the top floor of the Chicago Athletic Club. Take the elevator up and enjoy a beer with a view of Millennium Park.

8. City Winery at the Chicago Riverwalk

This is the perfect place to grab a drink at sunset!

9. RL Restaurant

If you’re shopping on the magnificent mile get a reservation at RL Resturant- Classy and Delicious.


1. Cloud Gate

Obviously, Cloud gate/ “The Bean” should be your first stop when you get to Chicago. It’s a sight to see. My favorite part was walking underneath and looking up.

2. Buckingham Fountain

Buckingham Fountain is a short walk from the bean and a great photo opportunity.

3. Garfield Park Conservatory

We didn’t have time to visit this garden, but it looks amazing and I really wanted to visit!

4. Wendella Boats

When in Chicago you have to do an architecture tour on the river. We booked tickets trough Wendella Boats and had a blast.

5. Ohio Street Beach

I had no idea Chicago had beaches! If you visit during the summer definitely bring your swimsuit.

6. The Art Institute of Chicago

Museums are usually to slow pace for my vacation mode, but we stopped at The Art Institute of Chicago and really enjoyed it!

TIP: Enter on Monroe street to avoid the long lines!

7. Jay Pritzker Pavilion

We had the best time at a free concert at Millennium Park. Check online before you go to Chicago and see what concerts are offered.

8. Bike Ride

You can rent bikes for $6/30 minutes through Divvy bikes. I mapped out the bike route we took on the map.

And that’s a wrap! I hope you enjoyed this city guide to Chicago!




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