How to plan a weekend in Chicago for $400

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Want a cheap weekend stay in a great city with lots of options to entertain the kids? Find out how to plan a weekend in Chicago for $400.

Chicago doesn’t have to be expensive. You just have to know how to plan for it. We love spending a long weekend in Chicago. In fact, we go there so much that we have our ‘usual’ places to visit.

Chicago is great for kids, too! There are so many exciting and new places to visit. Check out 7 things to do with kids in Chicago for some educational and fun destinations.

Millenium Park Chicago
Enjoying the day in Chicago’s Millenium Park
Chicago's Millenium Park
Beautiful day in Chicago’s Millenium Park

But, are you worried about the cost of going to a big city? Let me show you our most recent trip itinerary. It doesn’t have to be expensive! If I can do it, so can you. You just need to know where and when to look.

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Honestly, for this trip, I just paid cash. I had a couple of Southwest gift cards and I found a deal too good to pass up. Sometimes, that’s how I plan my vacations. We go where the airfare is cheap!

A couple months back, I jumped on a Southwest sale (I subscribe to their email list) and bought round-trip tickets for my husband, daughter and myself. Fares were $98 each at the time. Since I have the Southwest Companion pass (my all-time favorite credit card bonus), my daughter flies free with me until the end of this year.

Airfare total = $196.


Chicago has no shortage of hotels that’s for sure. But, for this trip, I wanted something inexpensive. We have stayed in the Loop district, on Michigan Avenue, on the River and near Watertower.   On this occasion, we did something different. We stayed at an airport hotel.

Southwest flies into Midway Airport opposed to the much larger O’hare airport. A new Hyatt Place at Midway opened in 2016. As I was browsing the available rooms, I realized I was able to book a suite for the same price in points a normal hotel room would cost.

A suite! I love the extra room. I love having a door to the bedroom. While the majority of Hyatt Place hotels are 5,000 points per night, this one was the next category up at 8,000 points. In contrast, a standard room at either Hyatt Centric in the city would cost 20,000 points each night. The Hyatt Place hotels include free breakfast, too.

I decided to go with the extra square footage at a lower price point. However, this meant taking the train into and out of the city each day. We only spent two full days in Chicago, so I thought going with the lower price outweighed the inconvenience.

I used 24,000 Hyatt points for our stay, therefore my out of pocket cost was $0. This is where having the Chase Hyatt credit card comes in handy. I love my Hyatt points and frequently use them for our hotel stays. Currently, the Chase Hyatt credit card comes with a 40,000 point signup bonus.

Hotel = $0


Of our two days in the city, the weather was only looking favorable for only one of them. The second day showed rain and thunderstorms which meant we needed to find indoor activities. With that in mind, I knew that museums were in our plans.

In my opinion, the Chicago museums are quite pricey at $25-35 per person, depending on where you go. This is where I like the value of a Go City card. The day before we left, I purchased the Go Chicago Explorer card for 3 attractions.

I knew I wanted to take an architecture cruise (included in the card) and then we could go to two different museums on our last day. This pass does give you a variety of 25 options from which to choose. Both the Adler Planetarium and the Field Museum are included choices and are near each other on Chicago’s Museum Campus.

Go Chicago Explorer cards (2 adults, 1 child) = $199

Are you interested in scoring a long weekend getaway on a budget? Don’t overlook the value that travel reward credit cards can bring you. On this trip, I used my Chase Hyatt Visa points to pay for our hotel stay. I could have used Southwest points from either the Chase Southwest Premier or the Chase Southwest Plus credit cards, but I opted to pay cash for our airfare instead because of the inexpensive price.

It really is a reality that people can travel for pennies on the dollar when they use some type of travel reward currency. Don’t be afraid of these cards. As I mentioned in Miles and Points 101, you need to pay off these credit cards every month. Then, enjoy the benefits and have a great time with your family reaping those rewards!

Do you have any vacation spots you consider your second home? What is your favorite weekend getaway? Let me know in the comments!

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