Chicago: Part 1 (Lodging, Transportation, Food)

Our nine-year wedding anniversary rolled around last week. Calvin had casually mentioned just doing a joint thing, nice restaurant, no gifts etc. I should have known he had something in the works. And that something was a four-day adventure to Chicagoland.

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Calvin and I love a bargain, so it’s fitting that this Chicago review is full of budget friendly tips and deals. Leaving room for things like a quick trip to ZARA for some Summer essentials. Here is a run down of all the deals and all the fun.

Lodging: Hotels in Chicago, especially in Spring and early Summer, are outrageous. We utilized AirBnB to get a great deal on a studio apartment. The apartment had more room than a hotel room, a full kitchen, a record player(!) and it was close to an L station. (More on the “L” in a bit.) Our host even had fresh towels and toiletries in a basket waiting for us. We also enjoyed living like “city people” rather than staying in just another hotel. Adds to the authentic adventure feel.

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Transportation: Last November, we signed up for a Southwest Visa credit card to take advantage of the 50,000 miles sign-up offer. This can be equivalent to about 3-4 round trip flights if used correctly. For this trip, we went ahead and used points (you still have to pay the taxes) . Right now if you sign up for a Southwest credit card you can still get 50,000 points if you spend $2,000 in the first 3 months of opening your account. We use our credit card like cash for our regular purchases (gas, groceries etc) and pay it off monthly. The rewards are valuable if you can discipline your spending to use it correctly. We did not rent a car in Chicago. The “L” which is a cool train transit line took us everywhere we needed to go. We took it from the airport to the apt and then all over the city. We purchased a 3 day-pass for $20 each. So for $40 each we had all the transportation we needed to navigate Chicago easily. The Google Maps app took out all the intimidation of public transportation. It gives  step-by-step instructions for the L and bus system as well as ETAs for the train stops.

      FYI: Southwest currently has (as low as) $116 one-way tickets to Chicago! Ends tomorrow 6/18/2015

Food: We really didn’t have to over-think the food situation. There are great restaurants in all the little neighborhoods that make up Chicago, you can easily find a great hot dog, pizza, or Italian beef sandwich. Definitely check Groupon ahead of time and download their app for local food deals. On the night we saw the Blue Man Group, we purchased a Groupon for Four Belly (asian street food) ahead of time since it was down the street from the theater. Our biggest money saver was a new program called Spring Rewards (Nashville folks – The link is for free $10 to Sky Blue Cafe for signing up). Through Spring Rewards, we saved about $80 on food. Many of our meals ended up being $3-$8 after tip!

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I personally love Spring Rewards because I didn’t have to hand the waiter a coupon or voucher, show my phone etc. We pre-loaded the deals into our account and the money was credited back to us from Spring Rewards. For example, we had a $15 (receive $15 back when you spend $15 or more) Spring Reward for a sushi restaurant. We went in, ordered a couple of rolls for an early dinner and spent $15.35. We tipped the waiter accordingly and we received the email moments later that a $15 refund was on the way. We used Spring Rewards to get lunches at little to no cost and also used this method to eat dinner by “restaurant hopping” having smaller meals at 2-3 restaurants. It was a fun challenge and a way to try several places.

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Our one splurge was at The Purple Pig which is located on the Magnificent Mile. It was apparently voted as one of the top 10 restaurants in America by Bon Appetit. And yes. It was amazing. Definitely put it on your splurge list for Chicago. We ordered small plate items and shared and still got out just under $40.

General: I have definitely fallen in love with Chicago. I know some may disagree, but I saw a lot of warmth in the people there. I saw people give up seats on the L for women with babies, I saw people chat and communicate with strangers who looked very different from them. I watched blind adults navigate the public transit system. So much diversity and respect for others. I think maybe I’m just in love with public transportation… but still, I saw some great stuff on there. Another thing I love about Chicago is that it’s not ragingly expensive. No $20 hamburgers! Everything seemed to cost about what we would see in Nashville. We even ate deep dish pizza at the famed Pequod’s pizza for $4.99. I would call Chicago, the no fuss city. Just come as you are, enjoy the city, enjoy some art, enjoy some food. Can’t wait to go back.

Part 2 of our Chicago review is coming later this week! We will be sharing about the activities, attractions and sites we enjoyed while in Chicago.

About the author

Erica

Erica is an advocate for simplicity, family time, making a cozy home and loving others well. She is the community coordinator for One Orphan, the orphan care ministry of America World Adoption Association. Erica and Calvin have four young children; Elliott, Charlotte, Lola and Liam. They currently reside in Nashville, TN.

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