North America,  Travel

Tips on Weekend Travel – Chicago Ed.

While I haven’t explored enough of the world yet to feel thoroughly committed to saying one city is my favorite – Chicago comes pretty close. David and I are both big-city people at heart, who also just so happen to be lucky enough to live right next door to one of America’s major hubs.

The word “wanderlust” makes me want to throw up due to it being saturated in cliche’, but if you are like me and feel antsy when sitting still in one place, I would suggest to you one option: weekend travel. Go someplace close! Travel to that one-hour away winery you’ve been meaning to go to. Hit up the historical site or landmark you missed on that field trip as a kid. See your state’s capitol. Hold onto your vacation days like Scrooge for that big trip you reeeally want to take, and satisfy your immediate travel craving by popping by somewhere close.

With dreams to possibly some day move there, David and I travel to Chicago for vacation purposes pretty frequently. Last year alone, I believe we went 4 times. Our excessive trips have made us prime candidates for questions from the less traveled, with inquiries into how we afford it, why we like it so much, and what we do. I have compiled and condensed a small list of FAQ and hope that I can assist you in a cost-effective weekend trip as well!

  • How will I get there?

First of all: for the love of god, leave your car at home. Chicago is a magical, reversal world where your normally beloved and reliable car will end up becoming a hassle. There is traffic. There is expensive parking. There are outrageously priced Illinois gas stations. And there are an abundance of other transportation methods that will make your stay simpler, better for the environment, and cheaper.

If you’re coming from St. Louis or a surrounding city of CHI, my recommended method of arriving is to take the Greyhound bus. They are by far the most affordable option, and additionally offer several stellar promotions throughout the year. You can get discounts by being a student, by being over 65, and just for signing up for their emails.

If you are looking for a more scenic travel option, my next suggestion would be Amtrak. Amtrak is also plenty inexpensive, with a great student discount as well. Sometimes these seats can be as low as $27 one way (you’d definitely spend more on gas to get there) and you have the mobility to get up and walk around the train and use the bathroom. The best part about riding Amtrak though is that it (STL -> CHI) is almost the same travel time as being in a car.

Be sure to check out your employer benefits or other memberships too, such as AAA, for deals. David and I looked into this and have been able to ride Amtrak for free or close to free several times now. Score!

  • Okay – I am here without my car. How do I get around?

Goals & Garbage - A photo of brunch at Hutch American Bistro in Chicago, IllinoisIf you are from St. Louis, or another city with a poor transit system, prepare to wipe a few tears away from your eyes. You are in the land of the Chicago L. Now is the time to grab your Ventra card, load it up for the weekend, and begin scootin’ around. At the current time (April 2017) a 1-day CTA Line pass costs only a mere $10, and a 3-day pass is $20. You definitely would have spent more on parking your car in the hotel lot.

Perhaps, again if you’re from St. Louis, you are a bit nervous about utilizing transit. St. Louis’s metro system doesn’t have the best reputation, both in terms of crime rate and reliability. To answer these fears:

  1.  Chicago’s metro will not let you down, time wise. If you miss a bus towards the city center, you will likely have to wait on average 7-11 minutes for the next one – depending on the day. Not an hour and a half like in St. Louis.
  2. As for crime: it is always a good idea to be aware of your surroundings and keep valuables out of sight. However, Chicago’s main lines closer to the city are bustling with people and typically protected with CTA employees during day time hours.

If you are not used to public transportation, you will feel out of your element momentarily. But with a few quick rides, you will most certainly get the hang of it and feel #blessed to have not brought your own clunker to try and get around in. There are several apps out there that will help you find your way to stations and estimate how much time you will spend on board. Google Maps is one of them – I bet you already have it on your phone right now!

There may be some instances where the CTA may not be a viable option. My next suggestion would then be to use Uber, Lyft, or if you are feeling fancy – a cab.

  • How should I save on where to stay?

Your cheapest option in Chicago (or anywhere) will be to stay with a friend for free. No friend to stay with? Next stop would potentially be a hostel. These are good choices if you’re an adventurous couple who want zero alone time or are traveling solo.

For David and I, these two ideas were off the table. We have friends in Chicago, but none of whom have a place for us to sleep. And as for the hostel – the one I linked to is not co-ed, and therefore would still not make financial sense for the two of us.

If these options don’t appeal to you, my next suggestion would then normally be to rent an AirBnb. In Chicago, however, with the cleaning fee, the service fee, and the OUTRAGEOUS hotel occupancy tax, an (entire home/apt) AirBnb becomes just as expensive as a hotel. Only with no additional baggage check and less amenities (which is important if you want to leave your shit somewhere while you explore the city on your last day!).

This leaves you with your final option: finding a hotel. Hotel’s and I aren’t great companions. As a hostel hopper during my 6-month stint in Europe, a generally big fan of AirBnb, and not one to turn my nose up at a Super 8 stay, I try to avoid hotels. A fancy room every so often is nice, of course, but in my opinion saving money typically trumps 4 star hotels (speaking of – don’t stay at the Trump hotel). Chicago is the only city I make exceptions in and I always score a great deal on a place to stay. Here’s how:

  1. Google “hotel deals in Chicago” and adjust the date to the days you’ll be staying. Sort by price. Now use the map to scan the area you’ll want to be staying in, and search out your cheapest option. Note: Absolutely make sure to do this both on your mobile device, as well as on a computer, as deals will vary.
  2. Next, be sure to scope out the budget sites., Kayak, Expedia, Groupon, etc. Google will most likely show you these deals on their listings, but it is always good to check.
  3. Screen shot everything. If you find a good deal, take a snap of it or it could be lost forever!
  4. Join rewards programs. They will email you when they are having deals, and if you rack up enough stays somewhere, they offer rooms for free or discounted prices.
  5. If you find a phenomenal deal – book it. For the weekend, anything under $100 is a steal, and anything in the $125 range is fair. If you don’t find anything too appealing, however, wait. Hotels adjust their prices all of the time, so if you’re planning ahead, feel free to give it a day or two, or even a week, to marinate.
  6. Call and negotiate. This might feel uncomfortable for people who are shy about asking for discounts. Here is where I tell you to suck it up. The worst that can happen is that they will tell you no, and that’s okay!
    Most hotels will price match competitors deals or what you find on third party sites. So those prices above I told you to screen shot? Bring those up. What’s even better is when you call a hotel, you often might find a deal that is not listed on their website.
    Examples: On New Years Eve, I found a deal for a hotel at the Kimpton. When I went to book it online, the website kept giving me errors. I ended up calling them, and they told me they had one slot open left for a promotion they were running, and asked if I wanted the room. I ended up only paying $89.00 a night at a 4 star hotel over a holiday weekend!
    Another example: At the Warwick Allerton, they had removed a promotion they were running from their desktop website, but forgot to remove it from their mobile website. When I asked if they would give me the promotion price as they were still advertising, they asked for proof. Lucky for me, I had a screen shot of their error and I emailed it to them. Guess who ended up with the promotional price.
  • Alright then. So what’s there to do on the cheap for a young, broke, millennial couple?

There is so much to do in Chicago, that if you truly are just stopping in for a weekend, it is a good idea to plan ahead of time what you must do and what you can miss. Here, I detail touristy and non-touristy options for the thrifty sort:


  1. Walk to Navy Pier and explore, then walk down to Millennium Park (or vice versa, depending). If it is a nice time of the year, bring your bathing suit with some snacks and hang out on the beach.
  2. If you are a newcomer, or really just enjoy being a tourist, check out the Bean, located in Millennium Park as well.
  3. Be impressed by the height of the Willis Tower by walking past it and not paying $23 to go up in it.
  4. Check out the free Lincoln Park Zoo! Of course, if you’re from St. Louis you might be too hoity-toity for this. After all, your free zoo was voted the best in the US for two years in a row now.
  5. Window shop on Michigan Avenue. Maybe splurge on an ice cream at the Hershey store, or wander into Forever 21 and buy a denim jacket (guilty).

For cheap-cheap:

  1. Thrift shop in Wicker Park and Logan Square! David and I’s favorite neighborhoods in all of Chi. Welcome to your hipster mecca.
  2. See an improv show at IO and marvel at the fact you are standing in the same place Amy Poehler once stood.
  3. Eat. Everything. Deep dish is a must for the Chicago virgin and make sure to carve time out for one of Chicago’s many glorious brunch spots. Here are my vegetarian recommendations: Native Foods, Chicago Diner, Handlebar, Kitchen 17 (they have vegan deep dish!), Sprinkles Cupcake ATM, Hutch (for $1 mimosas on the weekdays!) etc. etc. etc.
  4. Wash it all down with a cold beer. Our fave place to go is Emporium for the arcade games. Maybe you’ll run into a Chicago Tribune photographer and get featured in their newspaper, like we did.
  • In conclusion:

While I am not a travel agent, I hope I have provided you some valuable tips for your next (or first!) weekend excursion to the windy city.

Questions? Concerns? Disagreements? Suggestions? Please let me know all of your thoughts in the comments section.

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