Budget Trip To Chicago: Travel Hacks To Spend Less

Budget Trip To Chicago: Travel Hacks To Spend Less

Are you ready to start traveling again and thinking about a trip to Chicago?

Travel is on the rise and everyone is looking for the best places to spend their summer vacation.  You may have been able to save up some extra money over the past year but that doesn’t mean that you need to blow it all on one trip.

For our 5 day stay in Chicago we were able to travel hack by using airline miles and an Amtrak sale to travel between Seattle and Chicago.  We also used hotel points for our stay and used all the travel tips and tricks we could think of for budget dining and entertainment.  

If you are looking to plan a trip to Chicago on the cheap or need to stick to a budget for your next vacation and are looking for some tried and true travel hacks then read on!

Disclosure: Some of the links below are affiliate links, meaning we will earn a commission if you decide to make a purchase through our link, at no additional cost to you.

Travel To Chicago from Seattle:

We booked our one way flight from Seattle to Chicago in April for a trip the first week in June.  Our goal for this flight was to use airline miles so we searched directly on airline websites that we have points for.  

Luckily we were flexible on dates and if this is the case for you as well, then definitely take advantage of the monthly price feature that most airlines have to find the best deal. 

By signing up for the American Express Delta Credit Card, we were able to accrue enough points for this flight. 

The cost for our flight from Seattle to Chicago for a family of four was $20 (the taxes and fees associated with using points).

Current American Express Offers:

10,000 miles after spending $500 in three months with their Blue Card


70,000 miles after spending $2000 in three months with their Gold Card.

So if we bought a one way flight to Chicago, how did we get back?

We decided to take a train ride from Chicago to Seattle.  We do have enough Amtrak points for this trip but instead found an amazing deal during a sale they were having at the time.  It made more sense to jump on this deal instead of using our points at this time. 

The total cost for a train trip from Chicago to Seattle (2 nights / 44 hours) was $200 for a family of four.  

If you are interested in taking a train trip we recommend the Bank of America Amtrak Guest Rewards World Mastercard to earn points.  They are currently offering 20,000 bonus points after spending $1000 in the first 90 days.  


  • For domestic travel, you should start looking for flights 1-3 months in advance. 
  • For international travel, you should start looking for flights 2-8 months in advance.
  • Use incognito mode and/or clear cookies when comparing prices, especially if you notice that a flight has suddenly increased in price during your search. 
  • The best day to purchase tickets: Tuesday, early in the morning. 
  • The best days to fly: Tuesday and Wednesday.  Occasionally Saturday.

Amtrak Travel Hack

  • The Amtrak website is not the most user friendly.  Call customer service with any questions and to easily book a trip.  They are really helpful and much faster than trying to navigate the website.  

Where to stay in Chicago:

For our hotel stay we (you guessed it) used points.  When planning this trip to Chicago we had several hotel options to choose from but at the time of booking, Marriott had a deal that included staying 4 nights and getting a 5th night free, so it was a no brainer to stay at a Marriott hotel. 

To earn points for this stay we used the Chase Marriott Bonvoy Credit Card.

Current Chase Marriott Credit Card Offers:

3 Free Nights after spending $1000 in three months with the Bonvoy Boundless Card ($95 annual fee)


1 Free Night after spending $500 in three months with the Bonvoy Bold Card

So where should you stay in Chicago? 

We stayed in Streeterville, which we highly recommend.  It is a great location that is walkable to many attractions, shopping, dining, public transportation, the Navy Pier, the Riverwalk, etc.  

A lot of people ask if Chicago is dangerous for tourists.  There was not one time that I ever felt unsafe or that it was dangerous.  And we walked everywhere or took public transportation when needed.  

The hotel that we chose is Aloft Chicago Mag Mile.  But there are tons of hotels in this area to choose from.  So research and find one that fits your needs and budget.

Review of Aloft Chicago Mag Mile: 

I would definitely stay here again and recommend it to others.  It was clean and updated with modern décor.  It was by no means fancy, but it was perfect for our family. 

A Pros/Cons List for Aloft Mag Mile Hotel In Chicago, Illinois

Hotel Travel Hacks:

  • When using points, go directly through the hotel website and first look for additional deals, such as free night stays, discounted dates, etc.  
  • If not using points use 3rd party sites to book or to compare
  1. Priceline
  2. Hotwire
  3. Kayak
  4. Expedia
  5. Travelocity
  6. Hotels.com
  • Read reviews before booking and look at actual hotel guest photos.  Most hotel website photos show you the best rooms, so that can sometimes be deceiving.  
  1. TripAdvisor
  2. Booking.com

Chicago Public Transportation

You might be wondering, “What is the best way to get around Chicago.”  

The answer is not with a car.  Unless you enjoy traffic, crazy streets, paying an arm and a leg for parking at your hotel, you should leave the car at home if possible. 

Public transportation is actually very easy to navigate in this city.  

Fire boat on the Chicago River with skyscrapers in the background
Chicago Riverwalk

What is the best way to get from O’Hare to downtown Chicago

If arriving at O’Hare International Airport it is very easy (and cheap!) to take the “EL.”

Transit (CTA) may not be the fastest route but it is the most cost effective way to get downtown, if that is where you are staying.  

From within the airport, just follow signs to the CTA station which is located in the lower concourse.  It can easily be accessed from Terminals 1, 2, and 3.  If you are in Terminal 5 you will have to take a free airport shuttle train to get to the station.  

The CTA blue line runs 24 hours and goes directly through downtown Chicago on it’s way south to Forest Park. O’hare is the end of the line so get on any train that you see loading.  

You can purchase a single ticket, day passes, or a Ventra Card, using cash or credit card at the kiosks.  

Fare from O’Hare to Downtown Chicago is $5 per person but children under 7 ride free.  

What is the easiest way to get around in downtown Chicago?

We used google maps to access our options.  If we were unable to walk to our destination then we took the “EL” or the bus.  Transit in Chicago is pretty straightforward and simple.  We did not really plan ahead and just paid cash at either the kiosks (for the “EL”) or directly on the bus ($2.50 per adult, children under 7 are free) upon entering. 

Chicago Public Transit Travel Hacks:

  • You will always find CTA employees to help answer your questions upon entering the stations.  The CTA employees wear orange vests.  Do not trust a random person in the station to help you unless you identify them as a CTA employee. 
  • If you are taking the bus in Chicago and need to pay cash, you must use exact change.  No change will be given back to you.  
  • Use Google Maps on your phone to make a plan to get from point A to point B.  You can also track exactly where you are on the train or bus so that you know when your stop is coming up. 

10 Free things to do in Chicago

There are always so many free or cheap things to do in every city, you just need to know where to find them. 

By staying in Streeterville, we were able to find a lot to do within walking distance.  Here are some of the best free things to do from our trip to Chicago:

1. Chicago Riverwalk

  • Go for a walk, people watch, and don’t forget to look up at all the beautiful buildings

2. Lincoln Park Zoo

  • 35 acre zoo that is FREE.  
  • Easy to take the bus from downtown Chicago.  The bus stops right at one of the zoo entrances. 

3. Lincoln Park  Conservatory

  • Adjacent to the Lincoln Park Zoo. Enjoy walking around to check out all of the beautiful flora.

4. Millenium Park

  • Cloud Gate (The Bean)
  • Crown Fountain
  • Lurie Garden
  • Boeing Galleries
  • The Jay Pritzker Pavilion  (free concerts from August to mid-September)

5. Maggie Daley Park Play Garden

  • If you have kids who love playgrounds then you must stop here.   This playground is AMAZING.  

6. The Navy Pier

  • Fireworks
  • Ferris Wheel and Rides ($)
  • Mini golf ($)
  • Restaurants and Beer Garden ($)
  • Children’s Museum ($)

7. The Magnificent Mile 

  • Take a stroll and window shop

8. The Lakeshore Trail

  • Run, walk, or bike this beautiful trail along Lake MIchigan

9. City Gallery at the Historic Water Tower

  • Free art gallery showcasing work from artists and photographers.  And the building itself is pretty neat to see too!

10. Free public beaches

  • There are many free public beaches right on Lake Michigan if you need to cool down on a hot day.
View of Chicago Skyline at Sunset from The Navy Pier
View of the Chicago Skyline from the Navy Pier

Additional Chicago Attractions To Put On Your List

A few other things that we did not get to do but that I would put on my list for our next trip to Chicago include:

  1. 360 Chicago Observation Deck.  Formally known as the John Hancock Observatory. 
  • Travel Hack: Instead of paying the $14-$21 to go to the Observation Deck, go to the restaurant on the 95th floor and enjoy a drink with the same view instead. 
  1. Chicago Architecture River Cruise
  • While walking around  Chicago you can’t help but notice how beautiful the buildings are.  Even if you are not an architecture buff, the Architecture cruise gets great reviews and you would get some pretty amazing views of the city from a boat.  
  1. Grant Park and Buckingham Fountain
  • We did not venture far enough south to Grant Park but this 319 acre park would be fun to check out.  

Wrigley Field And How To get Cubs Tickets

And of course, no trip to Chicago would be complete without a stop at Wrigley Field to see the Cubs play. 

Going to a professional baseball game can be a little on the expensive side for a family of four.  And the beginning of this season was even more difficult than usual to get tickets for a good price. 

We ordered our tickets throughVividSeats and paid $160 for 4 tickets.  Yes we were in the nosebleed section but we had no problem seeing the game and had a great time.  Jason even bare-handedly knocked down (and almost caught) a foul ball.

A Review of VividSeats:

The website is easy to navigate and purchasing tickets was simple.  The purchase price for tickets was better than going directly through the team’s website.  

The one downfall and the reason why we would probably not use VividSeats again is that we had to wait until the day before the game to actually get our tickets (electronically).  This is probably fine if you live near the ballpark and just want to buy some cheaper tickets.  But if you are on vacation or really want to go to a particular game, I would not rely on a system like this.  

Other ticket options, besides ordering directly through the team’s website/MLB include:

  1. Ticketmaster
  2. StubHub
  3. ScoreBig
  4. Ebay
Wrigley Field before a Cubs Game
Wrigley Field – Chicago, IL

How do you get to Wrigley Field?

The easiest way to get to Wrigley Field from downtown is to take the “EL.” The Red Line stops directly at Wrigley Field – Get off at the Addison Station.  

Alternate instructions upon getting on the train:  Follow the swarm of Cubs fans to the “EL” stop, off the train and to the ballpark. 

Wrigley Field Hacks:

  • You are allowed to take in sealed bottled water so definitely bring your own.
  • There is a bike valet service if you decide to bike to the game.
  • A personal amount of food brought into the ballpark in a disposable bag is allowed. 
  • There are bag restrictions in place – see website for details

Wrigley Field Rooftops

If you are making a trip to Wrigley Field and can’t get tickets or if you are with a large group and want to do something special.  You should check out the Wrigley Field Rooftops.  

I had no idea about this option until we were in the ballpark and saw them all around the outside of the stadium.  

The rooftops at Wrigley offer an all inclusive experience.  The price includes food, drinks, and a perfect view of the ballgame.  

This would make a fantastic gift for someone who loves baseball or for a bachelor/bachelorette party.  

You can find out more information and purchase these Cubs rooftop tickets HERE.  

Final Thoughts On Our Trip To Chicago On A Budget

Whether you are planning a trip to Chicago for a weekend getaway or a week long stay, you will not be disappointed with everything that this city has to offer. 

This was our first time here and we were very pleasantly surprised with the ease of public transportation, the number of fun attractions located downtown, and the general feel of the city.  

We were able to find a ton of budget friendly and family friendly events, parks, and activities to explore during our 5 night stay.  Going on vacation does not have to break the bank and can be as budget friendly as you need it to be. 

We recommend taking a trip to Chicago and seeing for yourself what a wonderful city it is.  

Did we miss any must see places in Chicago?  If there are places that you recommend that I did not mention, please leave them in the comments below so we can add them to our list for our next visit. 

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4 thoughts on “Budget Trip To Chicago: Travel Hacks To Spend Less

  1. I stayed in Chicago for a couple of days back in 2014 and I really enjoyed it. Now the accommodation was pricey so I went with Airbnb but still, it was difficult without points (I am living in Luxembourg right now so we do not have access to all those rewards programs, or at least it will take ages) to find something well-located at a decent price. Other than that great tips and I would surely go again 🙂

    1. Accommodations in big cities can be a little expensive sometimes, which is why we were happy to have had enough Marriott points to use. Airbnb is also a great option that often gets overlooked – It’s nice to have some extra space and a kitchen, which would cut down on cost of food. Happy to hear that you enjoyed your time there too!

  2. Chicago is one of my favorite cities in the country. Those hacks saved you a lot of money. The next time I visit, I’ll probably use points to book my flight and hotel.

    1. We loved Chicago and were pleasantly surprised by the number of free and low cost activities that the city has to offer. Using points for flights and hotels is so easy and is a great travel hack. Thanks for reading!

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