A Squared: The Best & Worst of Food Delivery in Chicago

Wednesday, March 15, 2017

The Best & Worst of Food Delivery in Chicago

As much as I love the Chicago restaurant scene and getting dressed up to go out on the town, I have always been a fan of a date night in. And especially during those last few exhausting months of pregnancy and during the last 10+ months of even more exhausting new motherhood, ordering dinner, a bottle of wine, and a movie at home has really become our go to date night option. And I can't say I hate it!

With as much as we have been ordering out in recent months I have become something of a Chicago food delivery aficionado. I have tried pretty much every service available in Chicago-- and there are a LOT of them out there these days! And boy, have I got a lot of opinions now! After several months of "research," I have compiled a comprehensive list for you here: the good, the bad, what to order, and which service to avoid... plus a few referral links for discounted delivery too!

Seamless & GrubHub
Pros: I'm lumping these two together because they are sister companies and the apps are almost identical. These apps offer a huge selection of restaurants so no matter what you're in the mood for-- from cold pressed juice to greasy pizza and from steak to sushi, they've likely got at least one restaurant on their list that offers it. And because they are so widely used, there are tons of user ratings available for the restaurants here and I use them religiously (only 4-star and up ratings for me!) to filter my searches when looking for new-to-me restaurants. They also offer scheduled ordering, which is a really nice option if you'd like to plan ahead for a future delivery.
Cons: They rarely offer deals or coupon codes, so scoop them up if/when you see one! Also, inconsistency can be a problem. I've had really great experiences getting delivery from these apps, some meh, and some bad ones too. Some orders have delivery tracking, some don't. Some orders arrive promptly, some take double the estimated amount of time... it all depends on your luck and how busy they are, I suppose. What I will say is that when I've had to call or email about order issues, these guys have always handled them professionally and with a refund or credit when warranted.
Where to Order From: Kuma's Corner or Kuma's Too. Their enormous burgers and oversized mac and cheese are amazing! And especially on a weekend, they're known for drawing a crowd and a long wait time to be seated so have Kuma's delivered to you instead.

Pros: Postmates allows you to get food delivered from virtually anywhere-- even fast food or fast casual places that you wouldn't necessarily consider for delivery like Chipotle or McDonald's. In my experience, the
couriers for this service are super friendly and they'll text you if they have questions about your order or if the food is taking longer than estimated to prepare. And while many food delivery apps allow delivery tracking, this one is definitely one of the most accurate: You can watch your courier's travel on a map starting from the time you place your order to the time it arrives at your door. Use my code FSVD here for free delivery for 7 days!
Con: Crazy high delivery fees! Like Uber, delivery charges can surge during peak hours. So, during a big game, snowstorm, or weekend night, look out! Delivery fees can easily escalate into the $10-$15+ range quickly, making that quick delivery dinner even more expensive than running out to your favorite fast casual spot.
Where to Order From: Chipotle, ha! Also, you can get Chicago favorites like Smoque BBQ and Pequod's Pizza delivered right to your door... even with a high delivery fee, there are nights when that certainly beats waiting 1 hour+ for a table at one of these popular places!

Pro: Caviar is probably one of my favorite delivery apps. They have a great selection of restaurants including many higher quality and trendy spots around the city. Their service is consistently good, the app is user friendly and includes actual photos of the dishes (this is seriously a game changer when you're scrolling through an online menu), and they're almost always running some kind of deal--either a coupon code or free or discounted delivery from select restaurants.
Get $10 off your first two orders using this link to sign up!
Con: I've only got one small con for this one. Caviar offers realtime order tracking like many other delivery apps, but sometimes theirs is a bit wonky with delivery estimates jumping from 22 minutes to 6 and then back up to 21 minutes, for example. It isn't a huge issue, but can make planning for your delivery a little challenging.
Where to Order From: Honey Butter Fried Chicken and The Budlong! When I had a fried chicken craving on a snowy night toward the end of pregnancy, discovering that Caviar would deliver from HBFC (get the pimiento mac and cheese) and The Budlong (for Alex's favorite Nashville-style hot chicken) was pretty much the highlight of that week for me. And we have ordered from both a few times since and are never disappointed.

Amazon Restaurants
Pro: This is a newer offering from Amazon designed to make your life even more convenient. Order food from local restaurants via the Prime Now app and have dinner delivered right to your door-- with no delivery fee! We have used this service to order a barbecue dinner from Chicago Q (our favorite white tablecloth BBQ "joint") and countless times for pizza from Roots. They also sent a text to let us know that the food was on its way with an option to track the delivery via realtime GPS.
Con: Just like Amazon's free and expedited shipping perks, you must be an Amazon Prime member to use this service. It's also a newer offering, so the restaurant selection is a bit slimmer than on other apps. There are also some kinks in their delivery tracking, where sometimes it tracks your order and sometimes the map shows no movement until your food just shows up.
Where to Order From: Our new go to spot for pizza, Roots Pizza. Their crust is the best, they offer tons of creative topping options, and the menu features some cool local chef-inspired pizzas like my favorite featuring butternut squash, Brussels sprouts and bacon. They also deliver prepared foods from Eataly!

Pro: The great thing about this service is that it allows you to have food delivered from tons of different restaurants, many of which do not partner with other delivery services. The app is easy to use and has great search/filter functionality. If you type in "BBQ," it will prompt you to decide if that is BBQ chicken, pork, wings, etc. You can also track your courier on a map so you have a realtime idea of when your food is arriving.
Get $15 off your first order here.
Con: My experience ordering via UberEATS has been very similar to my experience using Uber: On balance, the service is convenient. However, because you're relying on a randomly selected (and maybe not super vetted) person making a few extra bucks in their downtime to drive you (or in this case, your food) around the customer service experience can be spotty. And when it's bad, Uber customer service is just as lacking as it is if you've ever had to report a bad driver experience. On the one hand, we recently ordered pizza from Coalfire and the driver was prompt and polite. On another, we ordered dinner from Stella Barra Pizzeria and when I went out to pick up our food I realized that the pizza was missing completely. I told the driver, she told me Uber couldn't do anything, blamed the restaurant, told me to call them, and drove away. Stella Barra went out of their way to make up for the mistake, sending a new pizza and a gift card our way to apologize (and comping the cost of the second pizza and its delivery), but they were understandably frustrated with Uber. Our pizza was sitting there with the rest of our food and the driver neglected to double check the order and take it with her.
Where to Order From: Stella Barra Pizzeria, of course! Their pizza is amazing and they took such good care of us after our botched Uber order that I love them even more now.

Pros: Rewards points! I'm a fan of any brand that rewards its customers for their loyalty and delivery.com is one of them. Earn 20 points with every $1 spent on your order and redeem them for credits on future orders or for swag like a Roku or an iPad. delivery.com frequently emails out coupon codes for delivery discounts so there is almost always an active one available to use. And they have also started offering laundry and alcohol deliveries on top of food! Use this link to get $7 off your first delivery.
Cons: The selection of restaurants is not as high end or as diverse as some of the others on the list. There are a few local favorites available, but a lot more of your standard takeout pizza and Chinese offerings. The order tracking is also a little old school: You'll get one or two updates about your order via text message, but no realtime map tracking like you get in some of the other apps.
Where to Order From: We don't do sushi often, but when we do it's almost always from our go-to neighborhood spot Ukai-- and via delivery.com. And Irazu serves up amazing Costa Rican food.

Pros: This was one of the first online ordering options available in Chicago and I'm pretty sure that Alex and I used it the first night we lived in the city and ordered California Pizza Kitchen to eat while we unloaded boxes. Ahhh, memories. DiningIn.com offers delivery from some of the more well known and upscale downtown Chicago restaurants. So if you're looking for delivery from places like Carmines, River Roast, Michael Jordan's Steakhouse or Slurping Turtle then look to DiningIn.com. Also, if you are a Lettuce Entertain You rewards member, you can order from virtually any of their restaurants on this site and can also enter your Frequent Diner number at checkout to earn points with orders from any of their restaurants. Get rewarded for ordering in!
Cons: No app! And you thought delivery.com was old school... ;) DiningIn.com is strictly available via website, so the platform is pretty basic in what it offers and is not as easy to place orders when you're on the go.
Where to Order From: Any of the Lettuce Entertain You restaurants like Big Bowl, Osteria Via Stato, or Wildfire!

Pros: Full disclosure, I have only used this app for delivery twice. That said, I'm a fan. There's a great selection of restaurants available from fast casual to high end. The app is really easy to use with a search by Cuisine feature and a lot of free delivery options. They also offer an interesting order tracking system that tells you when your order was received, when they began preparing it, when your delivery person has arrived at the restaurant, and when they have departed with your order. There's no map, but this is about as close as you can get-- and I would mention that both of the times we used DoorDash our order arrived way ahead of schedule.
Free delivery on your first order using this link.
Cons: This one is lacking some of the info that makes the other apps really savvy. There aren't any ratings from other users displayed, which I find really helpful-- especially when ordering from a new-to-me restaurant.
Where to Order From: Taco Joint is one of our favorite spots for Mexican food in the city and they offer free delivery via DoorDash. This app is also great for restaurants known for big crowds and no reservations-- so you can enjoy your Big Star tacos or Coalfire pizza at home without the long wait!

Groupon to Go
Pros: There seem to be some good deals available at many of the restaurants they feature. And you've likely already got a Groupon account. Also, the burrito I ordered was pretty tasty.
Cons: Where to begin? First off, I've had some less than amazing experiences with Groupon as of late so I was already a little jaded when I tried Groupon to Go. The ordering system is so confusing. There is a lot to filter through and deals are advertised and they make it incredibly difficult to figure out how to redeem them. I placed an order from Asada Mexican Grill because they were advertising $4 burritos, however there was no instruction on how to redeem this deal and it wasn't applied to my order. The same goes for the emails Groupon kept sending me saying I had a $10 credit to use on Groupon To Go orders. After contacting their support team a few times and then escalating the issues, I did get reimbursed for the falsely advertised burrito discount along with a $5 credit to use on future... though with all these other great delivery services (with much better customer service when issues arise too) that's probably not going to happen again.
Where to Order From: I'd steer clear of this one in favor of one of the aforementioned apps.

Happy dining in! What's your go to delivery app?

This post contains affiliate links and I will be compensated if you make a purchase after clicking on my links.


  1. Thank you for this post!! Seriously. We moved to Avondale from the West Loop and I miss being able to walk to a ton of amazing restaurants (plus, it's winter and cold) so I've been wanting to get more adventurous with ordering delivery. We usually stick to pizza and Thai/Chinese food so knowing some other options is perfect.

    1. So glad you found it helpful-- and after much research, I have been pretty impressed by the variety that's available between all of these apps.

      I miss West Loop living too, but you've got Honey Butter Fried Chicken and Kuma's Corner in your new 'hood!

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