Trip Report: Use Miles For Two To Get To Chicago for Less Than $55
Originally, I was planning on going to Dubai this May for the Memorial weekend. However, with a change of plans I had to cancel my Dubai trip. Since I already had vacation booked. My girlfriend and I decided to take a weekend getaway to the windy city, Chicago. This report covers the cost for hotels, airfare, and ground transportation. Not for dining, activities and other travel expenses.
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Best Airline Awards to Get There:
There are two main airport at Chicago, one is Midway International Airport (MDW) or Chicago O’Hare International Airport (ORD). Midway is a central hub for Southwest so we decided to take advantage of our Companion Pass and use our southwest points to get there. There are a lot of award options to get there but the best airlines to redeem your points domestically would have to be Southwest and British Airways.
British Airways Avios = 9,000 to 20,000 avois + taxes/fees (Anywhere in US)
For British Airways Avios you would need to redeem these flights on American Airlines, a travel partner of BA. You would need to route through ORD instead of MDW.
Southwest Airlines = 25,000 points + taxes/fees (Anywhere in US)
All Southwest flights will route through MDW as that is the hub for Southwest.
There are other airlines but they won’t be as lucrative as these two. We took advantage of Southwest Airlines since San Jose International Airport (SJC) is a Southwest hub and we had the companion pass to go along with our points. We only used 31,136 RR miles + $22.40 in taxes and fees each for our flights.
I was able to find flights from SJC-MDW easily using Southwest’s search engine. You will definitely need to be flexible in your times because low award flights are very limited when it comes to finding availability. For an example Southwest will definitely charge more miles if flying on weekends or during holiday travel.
Where to stay:
Usually, I would go with Hyatt as my 1st choice of hotel. However, I went with Club Carlson as my first choice. The reason why I wanted to burn through Club Carlson points was because the perk of getting one night free night per award booking is going away starting June 1, 2015. Meaning the value of these points are going to significantly lose value because that was the biggest perk as to why I kept them. To get the extra free night you would need to book 2 nights in order to get the 2nd night free. Thus, you are paying 2 nights with 1 nights worth of points. There are only 4 Radisson Blu hotels in USA. One of those Radisson Blu happens to be in Chicago. We decided to check out the most luxurious brand of Club Carlson and see if it lived up to its name.
I had to book one more night extra at another hotel since we only planned to stay for 3 nights. I decided to check out the new Hyatt Centric Hotel in Chicago. So we burned through 15k Hyatt points to stay there. If we were to stay 4 nights then I would have booked them all with Club Carlson to maximize my redemption of taking advantage of the 1 free night per award booking.
Everything was easily accessible with the Chicago Transit Authority (CTA). We even took the CTA to/from our airport to hotel. Once you are in the downtown (loop) then everything is walkable or just a train ride away.