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Chicago: A Weekend in the Windy City

This past weekend I enjoyed a quick getaway to the Windy City to visit our daughter for Parent's Weekend. We walked 23,000 steps in just one day and had the most amazing time doing it. The bonus...most of what we did was totally free!

Chicago Greeters

If this is your first time visiting Chicago, click here and sign up for this FREE program. If this isn't your first time visiting Chicago, click here and sign up for this FREE program. If you live in Chicago, click here and sign up for this FREE program. Basically I think everyone should click here to sign up for the free program because the Chicago Greeter program is such a great way to see the city from a new, unique, and local perspective.

We spent about three hours with our Chicago Greeter (a volunteer named Stetson) checking out the sites near Millennium Park. We had the best time seeing Chicago from his eyes. He was knowledgeable, took us inside buildings and spaces we had previously walked right past, and filled our time with facts, tips, and stories. He clearly loves Chicago and it showed!

Details on the Chicago Greeter program

By registering for a Chicago Greeter visit, you will have the opportunity to see Chicago through a local's eyes. These free walks are led by a volunteer who "shares interesting facts, insider tips, and an authentic perspective on life in Chicago."

  • Chicago Greeters requests all guests register at least two weeks in advance of their visit

  • The program provides the ability to customize your experience - pick the neighborhood, places, interests that you want to see and your guide will do the rest

  • Meet at the agreed upon location wearing shoes that can go the distance

  • The experience typically lasts two to four hours

  • Each tour can accommodate parties up to six guests

  • Tours are available in over a dozen languages.

  • There is a strict no tipping policy

  • Book a visit here

The pictures below are some of the interesting sites we saw along our tour.

Garfield Park Conservatory

The Garfield Park Conservatory is one of the largest indoor conservatories in the nation! It is stunning...and totally free.

The Conservatory offers both indoor and outdoor gardens with space to sit and enjoy the views. We spent about an hour walking through the various rooms, greenhouses, and outdoor landscapes. Reservations are free and required to enter. Advanced reservations are easy to obtain using the website. Walk-up reservations are an option as long as space allows. There is a small gift shop which provides water, simple snacks, and souvenirs.

Chicago Neighborhoods

Chicago is comprised of many small neighborhoods each with a unique personality, population, shops, and restaurants. Each time we visit Chicago, we try to explore a new neighborhood.

During this weekend visit, we checked out the following:

This neighborhood is located around the six-corner intersection of North, Damen, and Milwaukee. The streets surrounding this intersection are filled with boutique as well as second hand shops, restaurants, and bars. Parking was available on the streets around the main intersection using the paytopark app. The Damen Blue Line stop on the L will get you to BuckTown.

Although not technically a neighborhood, Southport Avenue is another lively shopping and restaurant area on Chicago's north side. Boutique shops mingle with retailers like Kendra Scott, Lululemon, Yeti, and Anthropologie up and down Southport Avenue. In addition to the shopping, there is no shortage of places to stop for a bite to eat or a drink. Our favorites includes Corridor Brewery & Provisions, Crosby's Kitchen, and Tuco & Blondie. All of these offer outdoor or open air dining. Parking for Southport Avenue is available on the residential streets - we found free street parking but had to walk about five blocks. The closer to Southport Avenue, the higher the likelihood you will have to use the paytopark app. The Southport Brown Line stop on the L will get you to this area.

Also on the North Side, this community is home to a commercial district that hosts a large assortment of locally owned shops, restaurants, and bars. The Swedish American Museum can be found in this neighborhood as well. We love to stroll along the streets and window shop before stopping at our favorite tapas wine bar (Uvae Wine Bar and Fromagerie). The main corridor is located along N. Clark St. Parking is mostly on the residential streets surrounding N. Clark however there are a few paytopark lots as an option. The Berwyn Red Line stop on the L will get you to Andersonville.

Located along Lake Michigan, Evanston is one of our favorite northern Chicago neighborhoods. Evanston is home to a really cute downtown area. The community is very walkable and includes parks, churches, beautiful old homes, shops, restaurants, bars, as well as Northwestern University. We always stay in Evanston when visiting Chicago-land because there are hotels in all price points that are located within close proximity to the restaurants and coffee shops. The area is easy to access from Lake Shore and is just a 30 minute drive into downtown (traffic permitting!). Parking has never been a problem and is accessible street side, in paid lots, and on the paytopark app. Take the purple line (on the L) to get to Evanston.

The Chicago Lakefront Trail

The Chicago Lakefront Trail is an 18.5 mile mixed use trail along Lake Michigan shoreline. We love to spend time along the trail and consider it a must do when visiting Chicago. Visitors can walk, bike, skate, or run along the trail. The trail passes through seven neighborhoods including downtown making it easy for visitors to easily access beaches, parks, favorite attractions as well as beautiful views of the harbor and the skyline.

The trail is open 24 hours a day but the parks and beaches close daily at 11pm

Technically pedestrians have the right of way but be sure to look carefully as the bikers and skaters move fast!

Find a map and full listing of stops here.

Where We Stayed:

We typically stay in Evanston when traveling to Chicago. Our favorite hotel in Evanston is The Graduate. The rooms are so cute! The bar has fun cocktails. The service is outstanding - the valet knew our name after greeting us the first time and provided great restaurant recommendations! The location is perfect with easy walking to restaurants, parks, and coffee shops. Street parking or valet services are available as needed.

A less expensive option (also in Evanston) is the Holiday Inn Chicago-North Evanston, an IHG Hotel. The rooms are spacious and clean. Parking is relatively inexpensive in the attached and covered lot. The location is great for walking to restaurants, bars, and coffee shops.

When to Go:

Chicago is great in any season. It can be very cold and windy along the water so be sure to dress in layers and plan for the weather.

Is Chicago Safe?

Generally, Chicago is safe. However, it is a large city and as such does have crime. Each neighborhood is different and visitors should always be aware of his or her surroundings. When visiting Chicago, we recommend taking the typical city precautions - don't walk alone at night, park your vehicle in well-lit locations, ensure valuables are stored out of sight, be aware of your surroundings at all times, when using public transportation be aware and alert.

Getting Around:

The easiest way to get around Chicago is by public transport. The "L" and Metra are fairly easy to navigate, typically quicker than driving, and accessible. The regular fair for the L is $2.50 while the bus is $2.25. You can purchase your tickets on location via a kiosk or front load a Ventra Pass using the app. The Ventra app allows the user to check arrival and departure schedules, maps, and load/reload the Ventra Pass.

Chicago is also very pedestrian and bike friendly. Divvy Bike rentals are available throughout the city. The bike share program allows users to rent a traditional bike, an ebike, or a scooter. Bikes can be rented by the minute, by the day, or by the month with the swipe of a credit or debit card.

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