So, my husband and I are finally doing it! As in flying to another city for anniversary getaway. I’ve mentioned earlier that I wasn’t sure what place to pick. I looked at various options, but the biggest issue was lack of time. We can only leave kids for two nights.
Since my husband isn’t a huge fan of travel, I wanted to make it as easy on him as possible. That meant picking flights with no connections and leaving at a reasonable hour. So, no 6 AM departures or midnight arrivals. Drum roll, please…
We are flying to Chicago! Neither one of us has been to that city, and it’s about time we change that. We are going in the early fall, and Southwest hasn’t yet released the schedule for our dates. I didn’t really want to burn 25,000 AA miles per person, and the flights were running at $175 or more. But I have Spirit currency, a co-branded credit card, and early fall happens to qualify for off-peak roundtrip pricing of 5,000 miles per person. Bingo!
I checked and was able to find weekend non-stop flights, so my husband would only have to take one day off work. Tampa airport is very convenient to us, and departure times are decent. We are leaving in the morning and coming back in the evening, so it would give us almost three days to explore the city.
But what about lodging? Well, I have some IHG points I could use, but central hotels are quite expensive. We don’t plan on renting a car, so need a place smack in the middle of Chicago. That way, we could walk to restaurants or take public transportation. I did have 30,000 Wyndham points, and that amount would take care of 2 nights at any property in that chain. And there just happens to be a perfect place in Chicago: Wyndham Grand Chicago Riverfront
That’s what the total for two nights would have cost us but instead, I used 30,000 points from sign-up bonus on Wyndham credit card (read my post here). I could have transferred Ultimate Rewards to Hyatt program and redeem them for a place that runs at 20,000 Gold Passport points. My husband happens to have Diamond status in that chain, so we would get free breakfast and other benefits. Sounds like a no-brainer, right? Well, not to me. I can transfer 20,000 UR points to Southwest or cash them out for $200. I can’t say the same for Wyndham points.
So, this is how I’ve put together an almost $1,000 vacation getaway for a fraction of the cost. No, the trip is not free because I’ll have to shell out a total of $70 for our checked bag (both ways). Plus, I did have to pay a $69 annual fee on Wyndham credit card. Still, all things considered, how can you argue with value?
But the best part is: we’ll be doing our first flight getaway since having kids. One of my favorite movies of all time is “The Lake House” Anybody else? I must have seen it 10 times. Sure, the plot totally defies logic, but who cares? Sandra Bullock and Keanu Reeves in a movie, it just doesn’t get much better than that. One of my favorite parts is when Alex puts together a walking tour of Chicago: See it here on Youtube I just might try to convince my husband to follow the same route!
Who should consider Spirit credit card?
I’ve mentioned this program to one of my readers who happens to live near Dallas. Take a look at this Spirit coverage map:
As you can see, Dallas is one of Spirit hubs. That means many non-stop flights, and most of them qualify for 2,500-mile one-way pricing. Obviously, there are many restrictions, but with some work and flexibility, you can beat the House. I just did. Let’s take Dallas-Denver route. I’ll admit, I had a hard time finding 2,500 mile pricing, (and that’s where real value is). That said, it does exist:
As you can see, the departure time is reasonable, and some flights leave on the weekend. Believe it or not, I put in 5 passengers, so it’s possible to take an entire family for this ridiculously low price. Of course, you do have to pay for checked bags, and Spirit has a very colorful reputation. Still, if you can get safely where you need to go, this is an excellent option. My sister-in-law flew to Atlantic City and survived. The flights left on-time and Spirit delivered exactly what it promised for only 5,000 miles roundtrip.
To be clear, I don’t think Spirit is the ideal program for most families with kids in school. There are many caveats, not to mention fees galore. Still, it can be an excellent gap-filler and could allow you to conserve valuable Southwest points. Let’s say you have a choice of paying 10,000 Rapid Rewards or 5,000 Spirit miles. Even with bag fees and restrictions, the latter is a much better deal.
Spirit can be a great program for couple getaways. If your in-laws or relatives are able to watch the kids, you can leave any time 5,000 mile pricing is available. If you happen to fall in the category I’ve described, my advice is to consider Spirit credit card at some point in the future. You get 15,000 miles after just $1 purchase, which could potentially take care of 3 roundtrip tickets. Read my posts on Spirit program here and here
You might be able to get an offer that comes with $100 cash back after $500 in purchases. You can see it when making a reservation on Spirit.com and going to the last page before putting in payment details. You can also call 1.800.932.2775 and reference priority code VACE5Z (hat tip to Will at Doctorofcredit for finding it). This card doesn’t pay me referral, so there is no financial incentive to recommend it.
P.S. Readers, please, give me some tips for visiting Chicago! Any decent restaurants you can recommend?
Author: Leana
Leana is the founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.
We went for a romantic weekend in Chicago in fall of 2015. My first recommendation is not to forget about enjoying the hotel room and each other! You are kid free! Get some sleep! (That was the first thing we did!) We ate out at three places that we loved. None of them were cheap, but it might be worth a splurge since you’re in Chicago without kids and you got hotel and air virtually free! We had a great dinner at Bandera. We had a lunch at Rick Bayless’ restaurant Frontera. (I only eat at restaurants that end in “era” suffix). We just walked in to Frontera, but we were told by the waitress that we were lucky to just be able to walk in and that next time we should make reservations. It was exciting for me to go there, as I love Mexican food and cooking and am a big fan of his show. If you can’t afford a meal there, consider stopping in for a Margarita at the bar! And the Purple Pig is kind of cool. We got in there because we showed up at like 3PM. It’s kind of a tapas bar with big wooden tables, a heated patio and communal seating. Again, kind of expensive though, so I’d just go for a drink and soak up the ambience. There was also a late-night Italian restaurant that we were in when we saw a rat walk slowly through the middle of the room. Don’t go there.
@Amanda Thanks for the laugh! I needed it today. We definitely don’t want any rats walking slowly through dining room. 🙂 I’ll have to do some research on restaurants. We don’t have a lot to spend on this getaway, so I’ll have to be very careful. Thanks!
A must when in Chicago: Garrett Gourmet Popcorn! It was one of the highlights of our visit to the Windy City! Best popcorn I’ve ever had, and definitely within anyone’s budget. We were in line for about 30 minutes outside the store in the Magnificent Mile area on a Saturday afternoon, and I was thinking to myself “So much hassle for just popcorn?” But once we had a bite we knew it was worth it!
The Architectural Boat Tour is delightful and informative, highly recommended! Other must-sees: Millenium Park (the bean, Crown Fountain), and Grant Park (Buckingham Fountain). Of course, you can’t go to Chicago and not try its famous deep dish pizza 🙂
@TropicGal Hmm, popcorn? Now I have to try it to see what the fuss is all about! It’s like “Hyatt Vendome” of popcorn. I definitely plan to go to Millennium park and possibly do a boat tour. Man, I hope the weather cooperates. To be honest, I like thin crust pizza, but maybe I can be converted. Thanks for suggestions!
Sounds like a great trip! I have only been to Chicago once on business and didn’t get to see anything or do anything fun. Now after reading all these comments, I want to go!
@Nancy I know it! I want to go too. I just hope this trip doesn’t fall through. Well, check into this Spirit credit card and maybe do a getaway of your own! Look how many routes leave out of Dallas, including Orlando.
Building on what Erik said, we have eaten at restaurants by all three of those famous chefs. We love Girl and the Goat (Stephanie Izard’s). We are always wanting to go again! She now has a cafe that we haven’t yet tried. We loved our food at Topolo (Rick Bayless). We ate at graham Elliott’s which was a very unique experience but also very expensive. I think he closed his restaurant that we are at but he may have something new going on. There are truly a lot of great restaurants to try!
@Julie All of these places sound amazing! I’ll have to check the prices but hopefully, we can do at least one splurge. My husband loves food, and this is something he would appreciate. Now I just hope my kids don’t get sick on the day of the trip.
If you are interested in history, I recommend a great PBS documentary on the history of Chicago. It really informs how you view the historic downtown when visiting. Not sure if you can stream it online, but we got it from the library.
http://www.pbs.org/wgbh/amex/chicago/
@Tyler Thank you so much for the link! This is something I’m definitely interested in, and will make sure to watch the documentary. I’m embarrassed to admit it, but I know very little about Chicago history.
We go to Chicago at least once a year, although it is usually as a family and not as a couple. Consequently this means we normally stay out in the suburbs, because the luxury hotels near the office parks are usually empty on the weekends and thus rates can often be found sub-$100. We have considered staying downtown on points, but we drive and the cost of parking a car in the city for a day or two is pretty outrageous. If you plan on visiting any of the celebrity chef restaurants (i.e. Rick Bayless from “Mexico, One Plate at a Time”, Graham Elliott Bowles from “MasterChef”, Stephanie Izard from “Top Chef”, etc…there are many), I would advise making advance reservations, as far ahead as possible (go to your desired restaurant’s web site and find out when they start taking them). At the very least, you should leave enough time to eat at one of Rick Bayless’s Tortas Frontera locations inside O’Hare airport (I just checked and there is one in terminal 3 that Spirit uses). I used to fly through there several times a year and VFTW is right that it is one of the best airport restaurants in the country. It’s hard to say what to do without knowing your interests – the Art Institute has some famous works and is a good couples destination. I’ve been going to the Field Museum of Natural History and Museum of Science & Industry since I was young and still enjoy them now with my kids (the former has the most intact T-Rex skeleton ever found and the latter has a captured intact German WWII submarine, a full-size Zephyr streamliner train, and other cool exhibits on display). If the weather is nice, though, you will likely want to do something that is outside – check something like chicago.metromix.com to see what is going on. Your hotel is not far from the State/Lake transit station, which will be convenient to get to/from the airport and may be useful for tourist destinations (check maps, it may be easier/less hassle to walk or uber). You can use “tap to pay” contactless credit cards on the transit turnstiles, with a negligible convenience fee (look on your card for this symbol: http://tinyurl.com/hksgs8x ) instead of buying the CTA’s transit card for $5. I think Apple Pay on the iPhone 6 and later might also work because it uses NFC technology.
@Erik As always, I appreciate your tips immensely. I doubt we will be eating at celebrity chef restaurants. I would love to, but we are on a tight budget. Dia from The Deal Mommy blog has recommended a place, so we might try it. That Rick Bayless’s Tortas place you’ve mentioned sounds interesting, and we should be able to go there before our return flight.
As far as sightseeing goes, I love art but my husband doesn’t particularly care about it. Since he was kind enough to agree to do this trip, I’ll have to cater to his interests. So, looks like we’ll be going to Museum of Science and Industry. Actually, we should both enjoy it.
When it comes to transportation, we’ll probably take taxi to our hotel. Another option is to start pimping my Uber referral link. Hmm… 🙂
– Instead of paying tons of money to go to the observation decks at Hancock or Sears/Willis tower, pay for drinks at the bar on the 96th floor of the Hancock. Same wonderful view but with drinks!
– all of the museums are wonderful imo so if you have any interest, go for it!
– I love millennium park, Maggie Daly park area. The iconic bean photo opportunity.
– the architectural boat tour is wonderful
– navy pier is not a necessary stop
– Chicago is famous for improv so consider tickets to Second City! So many famous faces have started there.
@Julie Wow, thank you so much! I’ll keep your tips in mind. I hope we have time to do at least a few of those things.
I lived in Chicago for years, my husband grew up there and we are actually about to move back. We love Chicago (except the long winter…we have been loving Texas winters). I am happy to try to help with anything you have questions about. Chicago is famous for pizza, hot dogs and beefs. I like pizzeria due or Lou malnati’s for pizza, and portillos for hot dogs and beefs, al’s is also good for beefs. All these restaurants have downtown locations. I will come back and write more later!