Ranked the third largest city in the USA, Chicago attracts 52 million visitors every year. That owes to the renowned architecture, mind-blowing food scene, unique attractions, national and international connectivity, and naturally, its proximity to the beautiful Lake Michigan.

If you haven’t visited the Windy City yet, ask yourself why not.

A trip to a metropolis in the USA may be a big no-no for people who hate crowds, traffic and high prices for almost every other thing. But why fear when the #TravelSmart mindset is here. From transportation to experiences, I’ve covered all the ways you can save money and time on your next trip to Chi-town.

1. Transportation


Money saving starts at the very first step of your trip planning i.e., booking your travel to Chicago. A variety of carriers fly into the Chicago’s O’Hare airport, and if you follow the tips explained in this beginner’s guide to find cheap flights, you’ll find incredible deals with Spirit, Frontier or JetBlue. I swore by that guide and was able to snag a ticket for $56 each way from DC during the Labor Day Weekend!

If you plan to arrive by road, use Megabus and Greyhound that offer $1 bus fares if you can get the timing right. Use Wanderu to search for the best options for transportation by road.

Public Transportation

When in Chicago, why not make the most of the second largest public transit in the USA, aka the L or El train. It gets the name from the railway system that is elevated in several parts of the city. In a way, it also serves as a quirky attraction to some visitors.

Chicago El Train | Photo Credit: Jeffrey Czum

Here are some specific reasons why you should ditch the cabs and ride the El:

  1. A train ride on any of the 8 routes serving 145 stations in Chicago is available 24 hours.
  2. Unlimited ride passes cost only $10 for 1 day, $20 for 3 days and $28 for 7 days.
  3. The Blue Line of L runs between the Chicago O’Hare airport and downtown, covering about 20 miles in less than an hour saving 15 times more money than an Uber ride.

#TravelSmart Tip

Decide upon the mode of transportation in the city beforehand. While you could buy a train pass at several locations throughout the city, save yourself some time and effort by purchasing it at the airport station itself.

Free Trolley

In summers every year, the Navy Pier runs a trolley available to ride for no charge. The stops along the route are at walking distance to several top attractions. More information on hours of operation and bus stops can be found in this link.

Bike Share

“Experience Chicago in a whole new way” - that’s the punchline of Divvy Bike Share which has become a big deal over the last few years in Chicago. If you’re someone who loves to bike ride and explore every nook and corner of the city with a flexible schedule, this is the best mode of transportation for you.

Divvy Bike Share | Photo Credit: Vishal Shah

The concept is simple and easy. You pick a bike from one docking station and leave it at another. The Explorer Pass of Divvy is ideal for visitors. By paying just $15 per day, you get access to unlimited rides up to 3 hours per ride.

Passes can be bought via kiosks, but I highly recommend you to make the purchase through the app. You can then view the available stations in the app too and plan your next attractions accordingly.

2. Parking

I don’t recommend you to drive in Chicago on your day of exploration, especially if it’s a long weekend. But for any reason, if you have to, follow these suggestions.

Parking in Chicago

Parking in the Loop area

Whether you are a first time tourist or a returning visitor to Chicago, chances are that you will be visiting the Loop. Meters run 24x7 in this area of the downtown with an hourly rate of $6.50.

You’re better off parking at the Grant Park South Garage which is a large garage beneath the Grant Park. It only costs $12 on the weekend for almost 12 hours if bought via Spothero.

Park your car, explore the nearby attractions, use the free trolley mentioned earlier, and have a fun day out.

Validated Parking at Select Businesses

Many restaurants and stores provide validated parking if you spend for their products or services. Call them in advance and clarify so that you can plan accordingly.

Free Parking

A few neighborhoods in Chicago have free parking on weekends in residential locations. Many areas outside the Loop have free overnight parking from as early as 10 p.m. to as late as 8 a.m.

Find Cheap Parking with Apps

Use one of the following apps to find parking in Chicago

  1. SpotHero - perfect for garage parking
  2. ParkMobile - perfect for finding free street parking and street parking rates

You can read more about why I suggest using these apps in this blog.

Some other apps that are used by locals are ParkChicago and SpotAngels.

3. Things to Do

Chicago has so much to do that even a long weekend won't be enough for you to do it all. Allow me to present you with different ways to cover the best attractions of the city and not drop your bank balance down.

Free Sightseeing

A google search of “Top free things to do in Chicago” will return a long list and you may pass out trying to get through all of them especially during holidays and long weekends. I have curated a list of free attractions and added some insights just for you.

  • Cloud Gate aka The Bean: Strike off the most cliched yet impressive piece of architecture of Chicago super early in the morning, 8 a.m. latest. There will hardly be any crowds to disturb your Instagram capture.
  • Crowds at the Bean in the middle of the day

  • Jay Pritzker Pavilion: Free performances on Monday and Thursday evenings during the summer.
  • Jay Pritzker Pavilion

  • Museum Campus: Incredible skyline views of Chicago from here. You can choose to visit the museums here using the tips in the following sections.
  • Skyline View from Museum Campus

  • Navy Pier: A fun harbor area where you can spend an evening watching the sunset and enjoying the fireworks on Wednesday and Saturday nights.
  • Navy Pier

  • Chicago Riverwalk: Observe the architectural marvels along the Chicago river walking along this paved pathway.
  • Buckingham Fountain: One of the top 10 fountains in the USA showcasing a glorious water display every hour, coupled with a lights display when dark.
  • Chicago Cultural Center: An embellished building inside of which you can attend dance, music and theatrical performances, free of cost. Check their schedule in advance here.
  • Magnificent Mile: A dream come true for the window shoppers. This is the place to get the real downtown feels with the towering highrises.
  • John Hancock Center at Mag Mile

  • Lincoln Park: It is comparable to the Central Park of Manhattan with one major exception. The zoo inside the park does not charge an entry fee.
  • (BONUS) Maggie Daley Park: As an adult, simply relax and watch the kids play in this uniquely designed park with the Chicago skyline behind you.
  • Maggie Daley Park

#TravelSmart Tip

If you’ve still got time after doing everything on this list, ride the 606 with a bike to view the Chi-town suburbs.

Saving on Museum visits

Chicago has top-notch museums but entry to those come with a price. There are various ways to save at multiple museums throughout the city, which is why I have a dedicated section for museums in this guide.

Museums on Us by BofA

If you have a Bank of America credit or debit card, you can receive a free entry to select museums in Chicago on the first weekend of each month. The timing is perfect for those visiting Chicago on long weekends like Labor Day and Columbus Day. It also works out occasionally for the New Years and Independence Day weekends. The list of museums in Chicago covered under this program for 2019 are:

  1. Adler Planetarium
  2. Art Institute of Chicago
  3. View from the rooftop of Art Institute

    #TravelSmart Tip

    Not many people know this but you can visit the top of the Art Institute and have the view of the surrounding high rises to yourself.

  4. Shedd Aquarium
  5. Shedd Aquarium

  6. Chicago History Museum
  7. Museum of Contemporary Art
  8. National Veterans Art Museum
  9. National Hellenic Museum

#TravelSmart Tip

Your best bet to avoid long lines and save time in addition to the money would be to show up at the doors at least 15 minutes before the opening time. The more of these museums you can plan in the first quarter of the day, the lesser crowds you’ll face.

Free Museums

Many Chicago museums also have select days or hours of free entry for the general public. I have gathered a list of the ones you can prioritize to visit.

  1. McCormick Bridgehouse Museum on Sundays between May and October
  2. National Museum of Mexican Art every day
  3. National Veterans Art Museum every day
  4. Fed’s Museum every day
  5. Depaul Art Museum Wednesday to Sunday

Illinois Residents specials

If you’re an Illinois resident, you’ve got benefits you may not know about. A few museums allow free entrance on select days and hours to residents like you all year round. Just show up with a proof of residence such as a driver’s license and get in. This is the list I have rounded up with some top choices for you.

  1. Art Institute of Chicago on Thursday evenings from 5 to 8 p.m.
  2. History Museum on Tuesdays from 12 30 to 9 p.m.
  3. Shedd Aquarium - dates are updated on their website
  4. Adler Planetarium - dates are updated on their website
  5. Museum of Science and Industry - dates are updated on their website
  6. Field Museum - dates are updated on their website

Passes for Paid Attractions

If you are a fast-paced traveler that will cover everything we’ve discussed so far and wants to splurge on a few paid attractions too, I recommend you to purchase one of the tourists passes. The top two options are Explorer Pass and CityPASS.

Go Chicago Explorer Pass

Using the Explorer Pass, you will be able to visit 3, 4 or 5 attractions from a predefined list. You can even choose to build your own roster. Three of the most popular attractions offered are:

  1. Architecture River Cruise
  2. Architecture River Cruise

  3. Skydeck Chicago
  4. 360 CHICAGO Observation Deck
  5. View from 360 CHICAGO


The CityPASS is almost equivalent in cost to a 5-attractions explorer pass but provides a fixed list of quality attractions to visit. The best part about this pass is the priority entry to all of its attractions. That can make a serious difference if you’re visiting during the holidays.

The attractions included are:

  1. Shedd Aquarium
  2. Skydeck Chicago
  3. View from Skydeck Chicago

  4. Field Museum
  5. Adler Planetarium or Art Institute of Chicago
  6. 360 CHICAGO Observation Deck or Museum of Science and Industry

#TravelSmart Tip

For less crowded days, buy the Explorer Pass from Groupon that provides about a 10% discount on the actual price.

If you aren’t sure about the crowds, you can arrive at the destination, assess the line, and buy the CityPASS if needed.

#TravelSmart Tip for Chicago Observatories

  1. For at least one of the two observatories (360 CHICAGO and Skydeck Chicago), plan to arrive upstairs an hour before sunset and stay until it gets dark. That way you’ll get to experience the daytime, evening as well as the nighttime view. Make sure you account the waiting time to get upstairs.
  2. The hottest tourist activity in Chicago these days is to pose at the famous Ledge of Skydeck. However, the lines to get to the ledge can be excruciatingly long. If getting that insta picture is the goal, visit during the off-peak times, i.e., at opening hours and weekday afternoons.
  3. For an additional $8, 360 Chicago offers an experience known as the Tilt. After stepping on a glass window ledge, it slowly inclines outside of the tower. If you’ve experienced thrilling adventures (skydiving, helicopter rides, bungee jumping, etc.), you might find the Tilt super disappointing.

Tilt at 360 CHICAGO

Student Discounts

Being a Student sucks. You may have to do your own dishes or put up with your unpleasant roommate, but when you’re traveling in Chicago, being a student means saving money.

A bunch of the locations mentioned earlier provide student discounts to their entrance fees. Even pricey shows such as the Blue Man group and Broadway have student deals. Check out this exhaustive list on ways to save as a student in the city of Chicago.

#TravelSmart Tip

Technically, all you need to avail a student discount is to have a student ID with your photo on it. So if you’re a recent graduate who doesn’t look noticeably different since graduation, carrying around that ID will be worth a few extra dollars off.

City Festivals

Check for any festivals happening around the weekend of your travel. This website gives the most up-to-date calendar of all the events and festivals happening year round in Chicago. While some are paid, some have free entry and select ticketed experiences. A few noteworthy festivals with no tickets to enter include Taste of Chicago, Chicago Blues Festival, and Grant Park Music Concerts.

Chicago Greeter Program

This one of a kind program allows visitors to reserve a 2 to 4 hours tour in any of the neighborhoods of Chicago for absolutely no cost. Officially called Greeter Visits, these tours are conducted by knowledgeable locals who are volunteers and hence do not even need to be tipped. The visits need to be booked at least 10 days in advance to ensure timely scheduling. Click here to reserve your greeter visit.

#TravelSmart Tip

For those who don’t have confirmed travel reservations may benefit from the flexibility of the InstaGreeter program. You can just drop in and attend an hour long tour, again with no fee.

4. Food

Deep Dish Pizza

Deep Dish Pizza at Giordano’s

The most famous grub in Chicago is undoubtedly the deep dish pizza. There are plenty of restaurants in Chicago serving it, but as a first-timer, you should try it at two places at a minimum, Giordano’s and Lou Malnati’s Pizzeria.

You can conveniently schedule a wholesome pizza meal in your itinerary as both of these chains have over 40 locations each throughout the city.

Lou Malnati’s

Beyond Pizza

Take some time to tour the local food scene beyond the pizza. You can try a Chicago-style hot dog at Portillo’s or an Italian beef sandwich at Al’s Italian Beef.

The best way to try new menu items without spending much in Chicago is to use Groupon. While the Groupon deals give you a direct discount, Groupon Cashback will return a percentage of the paid amount to your card. Use this link to find restaurants, bars, bakeries, ice cream shops, tasting experiences and much more.

Another favorite way of locals to be economical with food and drinks is to visit places during happy hours. Here’s a link that you can use to find the best happy hours throughout Chicago.

Garrett Popcorn

#TravelSmart Tip

Garret Popcorn is usually listed as a must-try food item in Chicago, especially for the popcorn lovers. Before rushing into buying a bag of popcorn, sample a few flavors to ensure they are crisp and fresh.

5. Accommodation

Accommodation is the last section of this guide for a reason. I believe it is crucial to have a rough idea about the attractions you plan to visit before reserving your stay. This way, you have the flexibility to book a place that is well connected to most of the attractions on your itinerary.

I will not suggest you to travel to Chicago off season to save on accommodation like most might do. That’s because off season in this city is winter which is bitterly cold with nasty winds flowing from Lake Michigan. Since summers are the busiest for tourism in Chicago, try scheduling your trip at the beginning and end of the winter season to have more options with value prices.

Since Chicago is well connected by public transportation, staying at least 20 minutes out of downtown is the most reasonable choice one should make.

#TravelSmart Tip

One thing to note is that city and state taxes on vacation rentals are high in Chicago; it can go up to 23%. So compare all your options including the taxes and book in advance to get the best possible bang for the buck.

If you’re open to enjoy the hostel experience i.e. shared rooms, free breakfast, socializing opportunities, decent amenities, great proximity to attractions and local tips, all of that at an economical rate, pick your choice from Hostel World.

There are tons of Airbnbs too around the city which is why hosts post competitive prices. Follow these tips to find the right Airbnb as per your preferences.

So, what do you think? Are you inspired to travel to Chicago? If yes, make sure to come back and let us know how much could you see and do and in how much time.

Chicago Explorer