A weekend for two in Chicago, IL for $266: How I made it work


Trip length: 3 days

Number of people: 2

Total cost: $266

Vacation days used: 1

Chicago details

Click to enlarge

Why Chicago for a long weekend in October? Why not?! In reality, the impetus for this trip was the notification that US Bank’s Club Carlson credit card would no longer be offering the last night free on award stays as a perk. This perk was pretty much what made this card worthwhile in my eyes. Essentially, a two-night stay on award points could be had for half the cost. Knowing that this benefit would soon be cut (and wanting an October getaway of some sort), I booked up the swanky newish Radisson Blu Aqua Hotel Chicago for two nights for a total cost of 50,000 points. This hotel will now cost you 100,000 points for two nights. It’s probably one of the nicest (if not THE nicest) Radisson properties in the US, but I still don’t know that I would burn 100,000 points for two nights there. That’s a lot of points…

Radisson Blu Aqua

Unique architecture of the Radisson Blu Aqua

With the hotel covered, the next step was to book flights. Earlier this year, my boyfriend secured a Southwest Airlines Companion Pass by earning 110,000 Rapid Rewards points. This allows him to fly another person with him for free, whether on a paid or an award ticket. He booked these flights as an award, so we only paid taxes on the tickets.

Airfare and hotels essentially free, the only out of pocket costs we had were food and entertainment while in Chicago. The architecture boat tour was a must, being one of the highlights of the trip for me. We also managed to snag a couple seats in the Signature Lounge on the 96th floor of the Hancock building right around sunset. The views were absolutely stunning and worth the cost of the pricey drinks.

hancock building sunset

Unaltered photo of the sunset viewed from the Hancock building. Spectacular.

Tips to make it work:

  • The Southwest Companion Pass is a great tool for slashing the prices of domestic flights. The easiest way to rack up the 110,000 points needed for the pass is by signing up for two of the Chase Southwest credit cards when the bonuses are at 50,000 points. These sign up bonuses count toward the 110,000 points needed.
  • Both of Chicago’s airports are accessible by train. It’s the cheapest and one of the most convenient ways to get into downtown Chicago. A car rental is probably not worth the cost or hassle unless you have plans to drive out of the city.
  • For scenic views of Chicago, skip the $19+ tickets up the Willis Tower or to the 360° Observation Deck in the Hancock Building. Instead, take the FREE ride up to the Signature Lounge on the 96th floor of the Hancock building. You get, essentially, the same views you would from the observation deck plus you get to take them in while enjoying a cocktail. It’s a win-win in my book.
  • Take the architecture boat tour. It’s well worth the cost for the scenery alone, but it’s also highly informative and a lot of fun. Do it.
architecture boat tour

Gorgeous architecture abounds in Chicago (minus the tacky Trump logo)

In case you’re making excuses about the cost, $266 = about twelve workday lunches out. Pack your lunches instead and get traveling!