How to Spend a Weekend in the Chicago Loop

Weekend in Chicago

The Chicago Loop, is the center iconic playground for all ages. The Chicago Loop features plenty of things to do, eat and drink. In my opinion, whether you are visiting Chicago for first time or you have been to Chicago, it’s always fun to explore Chicago from the Loop. The Chicago loop has been very popular among locals, and visitors alike.

What’s Chicago Loop?

I bet, many of us, Chicagoans, do not know the real history behind the name “The Chicago Loop”. The Chicago Loop name initially came from the looping street carts in 1. Later those street carts were replaced by our today’s modern elevated trains, “L” trains. Today total seven CTA “L” train lines run around the center of Chicago, known as our “The Chicago Loop”.

The Chicago Loop is the place to begin journey as it features top museums, attractions, river and lake cruises, tours and many activities in and around the loop area. Everything is located in close proximity, within walking distance.

If you are planning to go further, then The “L” trains are the easiest way to get around the loop to get to your destination.

Before You Arrive

Chicagoans do not need a hotel unless they are planning to stay in the loop for the weekend. But visitors must book a hotel before arriving to the Chicago loop. There are over 89 hotels in and around the Chicago loop in downtown Chicago, but Chicago hotel room rates tends to skyrocket during peak season, especially weekend in Chicago.

Most important, I recommend to adjust your travel dates to make sure you get full two days in the Chicago Loop. You can refer my recommendations on top hotels near Art Institute of Chicago.

Weekend in Chicago : Day 1

Sightseeing Before Lunch

Millennium Park

Start your day at the Millennium Park. One of the popular landmarks in Chicago. At Millennium Park you can easily spend couple of hours exploring collection of art and world famous “The Bean”.

The Cloud Gate, the Metal Bean, is popular among Chicagoans and visitors alike. During summer season, there is always something going on at the Millennium Park. The Jay Pritzker pavilion hosts many concerts and music festivals throughout the summer. Consider to hangout later in the day to enjoy one of these music festivals.

Overall, there are many free things to do in Millennium Park including concerts, tours and family activities.

360 Chicago – TILT

Head to 360 Chicago, formerly known as John Hancock Observatory at 875 N Michigan Ave on 94th floor of the John Hancock Center. Enjoy breathtaking views of Chicago city, Lake Michigan and neighboring states.

360 Chicago features TILT – thrilling ride on 94th floor. It holds 8 people at time and tilt over the city from the 94th floor observation deck. You can enjoy drinks at the bar and cafe located at the Observation Deck.

I recommend 360 Chicago – TILT to add on your weekend in Chicago itinerary.

Admission to 360 TILT is included with Chicago City PASS and Go Chicago Card.

Lunch

If you are visiting Chicago first time then I recommend to try our Chicago Style deep-dish pizza. You can either go to Giordano’s loop location.

Giordano’s Loop Locations include 223 W Jackson Blvd and 130 E Randolph St by Millennium Park.

I recommend Giordano’s for their location close to the Millennium Park. But, you may also try Pizzeria Uno and Lou Malnati’s for deep dish pizza.

Sightseeing After Lunch

Mag Mile Shopping

Stroll through world famous Magnificent Mile on Michigan Ave. It is one of the upscale stretch on the Michigan Ave, starting from Chicago River to Oak Street.

Mag Mile features plenty of shopping and dining options in Chicago. Shop like celebrities on the Mag Mile.

The Chicago Riverwalk

The Chicago Riverwalk is fairly new attraction in Chicago, one of my favorite spot to hangout during happy hours. The Chicago Riverwalk is your play ground to eat, drink and enjoy activities.

I recommend Chicago Architecture River Cruise from the Chicago Riverwalk to first time Chicago visitors. Chicago’s First Lady Cruise, Wendella and Shoreline Sightseeing companies are popular for architecture river cruise.

In my opinion, you can spend entire day exploring the Chicago Riverwalk. You may like my guide on how to spend a day on the Chicago Riverwalk.

You do not want to miss the Chicago Riverwalk on your weekend in Chicago itinerary.

Dinner

There are so many good restaurants in the loop including historic restaurants such as the Berghoff Restaurant, The Walnut Room and Monk’s Pub.

I also recommend to explore State and Rush Street in the Near North Side neighborhood for dining and clubbing.

Our windy city is famous for theaters and live performances. If you are not into nightlife / clubbing then you can catch one of the shows at the historic Chicago Theater.

Chicago Theater features 3600-seat auditorium and hosts stage plays, magic shows, comedy, speeches and music concerts. I recommend to attend one of the performances or take a tour of the historic Chicago Theater. It’s worth visiting!

If you are planning to attend shows at theater then I recommend to reserve before you visit Chicago. During peak seasons you may not be able to get the tickets on the spot.

Weekend in Chicago : Day 2

Sightseeing Before Lunch

Museum of Science and Industry

Museum of Science and Industry is one of the largest and popular family friendly museum. Visit to Museum of Science and Industry is perfect for families with kids for learning experience while having fun.

It features award-winning exhibits. Visitors can explore both US-505 submarine and coal mine exhibit for additional fee. But, I recommend to spend little extra fee to explore US-505 German submarine and coal mine exhibit.

Admission to Museum of Science and Industry is included with Chicago City PASS and Go Chicago Card.

Museum of Science & Industry is located at 5700 S Lake Shore Dr, Chicago, IL 60637

The Art Institute of Chicago

The Art Institute is the second largest art museum in the country, with a collection of approximately 300,000 works of art and a physical space of nearly one million square feet. With an annual visitation of about 1.5 million, the Art Institute is one of the most popular attractions for Chicago residents and visitors alike.

The Art Institute is the most popular and second largest museum in the USA. Every year over 1.5 million people visit the Art Institute of Chicago to explore a collection of over 300,000 works of art.

I insist to visit once if you have at least little interest in art. At the Art Institute of Chicago, you can easily spend 2-3 hours exploring unique works of art.

Admission to Art Institute of Chicago is included with Chicago City PASS and Go Chicago Card

The Art Institute of Chicago is located at 111 S Michigan Ave, Chicago, IL 60603

Lunch

Chicago is famous for deep-dish pizza and Chicago style Hot-Dog. I recommend to try both Chicago style deep dish pizza and Hot-Dog to first time Chicago visitors.

Devil Dawgs is one of the famous and popular hot dog place in the loop, among visitors and locals alike. Devil Dawgs

Sightseeing After Lunch

Chicago Picasso at Daley Plaza

Chicago Picasso sculpture is located at the Daley Plaza, adjacent to the Richard J. Daley Center. The 50 feet tall Picasso sculpture gained attention through the controversy in the city, later it became Chicago’s one of the famous sculpture.

Daley Plaza hosts different kinds of festivals and events throughout the year. During summer it hosts Farmer’s Market and during winter it turns into Christkindlmarket, German Market.

Big Bus Tour

Whether you are planning to explore attractions or just want to drive around the downtown Chicago, Big Bus Tour is the best way to see all the best Chicago landmarks and attractions during your weekend in Chicago.

Chicago Big Bus Tour takes you around the downtown including top attractions such as John Hancock Center, Adler Planetarium, Soldier Field, Grant Park, Magnificent Mile, Navy Pier and more.

You can hop-off at any location to explore the attraction, and hop-on to get to the next designated stop. On Chicago Big Bus, you will be entertained by live guides sharing history and great stories of our Chicago architecture and culture.

The Grant Park Music Festival

Since 1935, The Grant Park Music Festival has been offering free entertainment to locals and visitors during summer season. It is most popular free outdoor music festival offering 10 weeks of free music concerts at the Jay Pritzker Pavilion in Millennium Park.

Whether you like the music or not, you are assured to have fun just even hanging out at the festival. There is always very live and energetic ambiance at the Grant Park Music Festival.

Buckingham Fountain

The Buckingham Fountain is one of the largest and popular historic fountain located in Grant Park. It runs from morning 9:00 am to 11:00 pm daily from May through October before the winter kicks in.

The Buckingham Fountain features center jet shooting water to a height of 150 feet into the air along with other water display for 20 minutes every hour. Personally, I like their last major display for the day at 10:35 pm.

Dinner

You can find plenty of dining options in the loop. The Potter’s Chicago Burger Bar is one of the best places to enjoy unique burgers in the loop. The Potter’s Chicago Burger Bar is located at Lobby Level of the Palmer House, a Hilton Hotel – 124 South Wabash Avenue, Chicago, Illinois 60603

When you spend a weekend in Chicago, I recommend to utilize one of Chicago attraction passes to save money and explore more without paying lot of money on admission.

You may also like my guide to spend 3 days in Chicago with kids.

Pin this to Pinterest:

Comments

comments