Boston & Chicago Master Post – Budget, Tips, and Final Thoughts

Let’s dive in:

Flight SFO > BOS: $180 (Delta)

Flight BOS > CHI: $120 (Southwest)

Flight CHI > OAK: $122 (Southwest)

Stay Beverly, 4 Nights: $259 (AirBnB)

Stay Cambridge, 1 Night: $90 (AirBnB)

Stay Chicago, 2 Nights: $0 (stayed with family)

Food, Shopping, Transportation, etc.: $729

Total Budget for one week: $1500



  1. You don’t have to stay in Boston Proper – we stayed in Beverly which is about 30 minutes away by train. We got to experience their commuter rail (so much more quiet that Bart) and saw more of the New England landscape. The downside is that a one-way ticket was around 7 dollars.
  2. Public transit in Boston is horrendous – I get it…the streets are windy and stop suddenly because the city grew organically instead of being planned out. This means it takes at least 3 buses to get anywhere. Be prepared to walk or uber…a lot. 
  3. The food ain’t great – very meh would be my final review. As my mom will say “Food is just better on the West Coast”. Photo above taken at Saus Boston.
  4. Do the cheesy stuff – I highly recommend one of the architectural boat tours in Chicago, I learned a lot and the views are amazing. Also the Freedom Trail in Boston was a great way to walk around and get a feeling for the city, there is an app you can download that could replace a guide and let you go at your own pace.
  5. I see dead people…you will see dead people. Ok, not really but there are cemeteries everywhere. And I am now convinced all of New England is haunted. Here is a picture of a black cat in a graveyard.
  6. Take a water taxi in Boston, esspeccialy from the airport. This kinda ties in with number 2, seriously it is the easiest way to get into town fast. Try Rowes Wharf Water Taxi.
  7. What’s the deal with no toilet seat covers? – Seriously…where are they and why don’t Chicago and Boston have them?


Overall, I am happy I took this trip since I saw two good friends get married, spent time with my cousin, and visited two new places. This trip also reminded me that you don’t have to like everywhere you go, sometimes you just don’t mesh with every city you go to. In this case, I just did not enjoy Boston that much but I looooooooooved Chicago. It can be hard to explain why but I like to say that people vibe with different places.


All Chicago and Boston Posts:

Shake Shack Dreams and Harvard Wanderings

Boston Cannoli Taste Test

Salem, MA –  A Visual Tour

New England Brews 

Boston Shopping – Primark

48 Hours in Chicago




Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s