• Rebecca Blackmon

3 Day Itinerary for a Weekend in Chicago

Hey guys! Our latest weekend getaway was in Chicago, Illinois for three days and two nights. We tried to keep the trip as cheap and budget-friendly as possible, so I wanted to share our experience!

3 Day Itinerary for a Weekend in Chicago Day 1:

Around 5 am on a Friday, we left Birmingham to drive to Atlanta. We arrived around 8am at Atlanta airport.

*PRO TIP: Make sure you check surrounding airports if you’re willing to drive a little bit. For us, the Atlanta airport is the closest really big international airport. Because it’s bigger it usually saves us a couple of hundred dollars to fly from there rather than Birmingham. Just make sure that you remember to weigh in the costs of gas and airport parking - for us, it was still cheaper to fly from Atlanta.

At 9:22 am we departed for Chicago and we landed around 11am in Chicago.

*PRO TIP #2: Since virtually everything is back open for the first time since before Covid, everyone is traveling. Do not assume that people are still staying home and security will be short. I can assure you, that is not the case! We made it through security with about 20 minutes before our flight was supposed to take off, and then we had to get on a train to get to our gate. Yes, we were those people we all love to make fun of running through the airport! We made it to our gate with slightly less than two minutes to spare before they closed the gates.

We stayed at the Warwick Hotel right on Michigan Avenue (basically where the Magnificent Mile is if you’re familiar with Chicago). We looked at multiple AirBnb’s and hotels, and this was the cheapest one. It’s a pretty old hotel so the rooms were very small - if you’re like us and don’t spend much time in the room when you travel it won’t matter, but if you like to stay in suites this wouldn’t be a good place for you. Other than size, though, it was a great hotel! We got there a little before noon and check in wasn’t until 4pm. They let us leave our luggage behind the desk so that we didn’t have to lug it all over the city which was super nice of them. Also remember that parking in Chicago is EXPENSIVE - the cheapest overnight garage we could find was $53 per night.

We had lunch at Flaco’s Tacos around 12:30pm. Flaco's Tacos was just walking distance from our hotel. The plates were about $10 each - tasty and affordable!

We walked around the Navy Pier from 1:30pm to about 3:30pm. By the way, the city has bikes for rent, much like the motorized scooters that a lot of cities have, but fair warning: traffic in Chicago is INSANE. I’m not great at riding a bike so I didn’t feel comfortable doing it there. We definitely saved money by walking, but if you’re confident in your bike riding skills, that might be the way to go.

We did not ride the big Ferris wheel because it was pretty cloudy, but had it been sunny we would have. It costs $15 to get a ticket, and reports say the ride lasts about 15 minutes. The park itself, though, is free to get into, so because we didn’t ride the Ferris wheel this was a free activity for us.

Around 3:30pm to 5:00pm, we walked back to the hotel, checked in, and got ready for dinner.

From 5:30pm to 7:30pm, we had dinner at Labriola Chicago. It was such a great find! We had plans to go somewhere else, but we walked by this restaurant and the pizza looked amazing. We went in on a whim, got seated right away, and only had to wait about 30 minutes for the food. If you're going to Chicago, Labriola is highly recommended for deep dish pizza.

At 8:00pm we went for a Chicago Gangsters and Ghosts Tour. This was one of my favorite activities of this trip! It was $27 per person but was totally worth it. It lasted almost 2 hours and the guide was great. It centered around the rise and fall of Al Capone, with some creepy ghost stories along the way. There was one stop for bathroom/refreshments and it was a great way to see the sights and learn about Chicago’s history.

We went back to the hotel after the tour. By the end of day 1, we had walked 10.5 miles. There were definitely opportunities for us to Uber and we chose to walk, but just be prepared and wear comfortable shoes!

3 Day Itinerary for a Weekend in Chicago Day 2:

We had our breakfast around 9:45am to 10:45am at Stan’s Donuts. The donuts were specialty donuts and they were delicious! There was a little bit of a wait, so plan accordingly if you choose to visit.

We went for a walk down the Magnificent Mile and went to take pictures at the Bean around 11am to 12pm. From there, we walked to get the car and drove to Wrigley Field (about a 30 minute drive) from where our car was parked.

We got to Wrigleyville around 1:00pm and walked around the stadium and the surrounding area. The Cubs were out of town this weekend but it was still so cool to walk around the stadium and see where they play! They do have the option of doing a guided stadium tour for $30, but we thought that was a little steep and chose not to do it.

Around 1:30pm, we went for lunch at Smoke Daddy BBQ. The place was right across the street from the stadium and the barbecue was delicious! We didn’t have to wait at all because the Cubs were out of town, but I loved the ambiance and I could just imagine how much fun it would be if there had been a game going on!

We drove back to the hotel around 3:00pm. We were really tired, we were starting to feel the 15miles of walking. So we rested, recouped and got ready for the night.

Starting at about 6:00pm, we played card games at the hotel and drank some Truly’s. The most expensive thing we came across by far in Chicago was the alcohol. If you’re on a budget and trying to save money, it will REALLY benefit you to buy some drinks from a Walgreen’s and drink a little bit before you leave your hotel!

We spent our dinner at Sushi-san. Because we ate a late, heavy lunch, we really wanted something light for dinner. We went with sushi (again, pretty last minute) and it was so good!

10:00pm-12:00am - Three Dots and a Dash, Howl at the Moon

*these were two bars in the downtown area that were recommended to us by a friend. Three Dots and a Dash is a Hawaiian/tiki themed speakeasy. It was such a cool vibe, but the drinks were REALLY expensive. The second place, Howl at the Moon, is a dueling piano bar. There are two pianos on stage and two people go back and forth playing songs requested by the audience. Both bars had a fairly long line waiting to get in - it seemed to be that way at every bar downtown.

By the end of day 2, we walked an additional 9 miles (19.5 miles total!).

3 Day Itinerary for a Weekend in Chicago Day 3:

We started packing to check out around 10am. We checked out at 12noon. We went for a brunch at Summer House. The restaurant was so cool! It was voted “Best Brunch in Chicago” so I definitely recommend making a reservation ahead of time.

We then spent about two and a half hours in Lincoln Park Zoo. The zoo in Chicago is totally free! It was one of the best zoos I’ve ever been to. It is also close to the Conservatory and Botanical Gardens, which are also free, but we didn’t have time to do them all. I highly recommend this if you’re traveling on a budget!

Around 4pm, we traveled to Chicago O’Hare International Airport and we flew back to Atlanta.

By the end of day three, we walked an additional 5.5 miles, which rounded out the trip total at 25 miles!

I hope this is helpful! Always remember - being on a budget doesn’t mean you can’t travel! It just means you have to plan ahead and find the free/cheap activities. In Chicago, those include: Navy Pier, the Bean, Magnificent Mile, the zoo, the conservatory, the botanical gardens, and a Gangsters and Ghosts tour.


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