TLDR: Chicago Holiday Trip
After spending the past two years on fantastic holiday trips to New York City, we decided to change things up and head to Chicago for Christmas. How would the Windy City compare to the Big Apple at Christmas time?
Festive lights, iconic holiday attractions, busy sidewalks? Check, check, check!
This trip was extra special because our son came along! Trent got to join us for his first holiday experience in a big city.
While hitting elite status was a major reason for originally booking the trip (I was 1 night short of Hyatt Globalist & 1 round trip short of Southwest A List), nothing could compare to having Trent along and sharing this winter wonderland together.
That said, we are EXTREME budget travelers. (Check out our cheap, luxury trip to Europe.)
Having Trent join us more than doubled our budget with the need for a second hotel room, a 3rd round-trip flight, and increased expenses in Chicago. (This boy eats ALOT!) But the memories we made as a family more than made up for the extra expense!
This itinerary is packed with festive fun and budget-friendly tips to help you make the most of your own Chicago holiday adventure.
Budget Overview
Speaking of our budget, we came in at $568 out of pocket for everything:
- 3 round trip flights on Southwest
- 2 hotel rooms for 2 nights at the fancy Chicago Athletic Association
- Food for 3 people for 2 1/2 days in downtown Chicago
- Entertainment (our 1 splurge)
- Local transportation (mostly rode CTA buses & the L)
If we were normal travelers, this 3-day, 2-night trip would have totaled $2,591. We saved over $2,000 on food, rooms, and flights thanks to our travel optimization techniques!
Get our Free 14 Page Guide to (Almost) Free Luxury Travel!
Hotel Location and Charm
We stayed at the Chicago Athletic Association, a grand old hotel located on Michigan Avenue, directly across from Millennium Park and right on the Loop for the L train. It’s a wonderfully restored historic building that was once the gathering place for Chicago’s upper crust.
Wrigley, Comiskey, Spalding, and Marshall Field are all names you know who helped shape Chicago’s identity, from sports to retail to industry. And they were all members of the Chicago Athletic Association.
While it may not be the most luxurious or swanky hotel we’ve ever stayed in (hello Park Hyatt NYC & Andaz Maui), the property’s charm, history, and location made it an absolute standout. It was fun to stay in a place that exuded the elegance of a bygone era while being so convenient for exploring the city.
What You’ll Find in This Post
In this post, we’ll share our 2-day Chicago holiday itinerary, packed with festive fun and tips for keeping travel affordable. As always, we aimed to minimize out-of-pocket costs while maximizing memorable experiences.
Travel Logistics
Saved 73% on Flights
We flew Southwest from Nashville to Midway, with Sandra’s ticket free thanks to the Companion Pass. Each leg of the flight cost her just $5.60 in taxes and fees. Trent’s flight from Nashville to Midway cost 7,034 points + $5.60, and mine was $47. Southwest’s A-List status ensured we got great boarding positions. And with 60 empty seats on the flight, we each enjoyed extra space.
Watching Trent’s face plastered against the window of an airplane never gets old. He’s an extra-large adult but he’s still a kid at heart, especially when he gets to fly!
In total, we spent $166 for 3 round trip flights. Without our Southwest Companion Pass tricks, this would have cost us $600!
Local Transportation
We opted for Chicago Transportation Authority passes to keep costs down. It was just $5 per person for unlimited CTA bus rides and rides on the L for 24 hours. Total cost: $30.
The Orange Line from Midway Airport got us downtown quickly. Along the way, we met Barry, a local who shared some great tips for our Chicago holiday visit.
Of the many tips from Barry, the standout was his suggestions that we visit the Billy Goat Tavern. That turned out to be one of Trent’s favorite highlights of the trip.
In addition to using public transportation, we used Lyft twice: once to get from our house to the Nashville airport and once in Chicago when there wasn’t a convenient bus schedule. Total spent on ride share: $67… but that earned us $25 in free travel.
Travel Optimization Tip
We chose Lyft over Uber because I earn 10 Chase points per dollar spent with my Chase Sapphire Reserve® card. We convert Chase points to Hyatt points which have an average value of 3.8 cents per point since we started traveling in 2021. That’s like getting 38% back on every Lyft ride.
Where To Stay
Chicago Athletic Association
This historic Hyatt property, located on Michigan Avenue right across from Millennium Park, was the perfect home base for our holiday itinerary. We booked two king rooms for 2 nights using 68,000 Hyatt points (saving over $1,600 in cash). As Globalists, we enjoyed perks like upgraded Millennium Park view rooms and AWESOME breakfast for free!
To ensure Trent received the same benefits, we used a Hyatt Guest of Honor award for his separate room.
The Chicago Athletic Association is truly a grand old hotel. Opened in 1873, it was once Chicago’s nicest building and a hub for the city’s wealthiest citizens.
The wonderful restoration of the building stays true to its original character, making it a unique and historic luxury experience. From the beautiful woodwork to the pommel horse benches, everything about this hotel exuded timeless charm.
Day 1 Itinerary: Christmas Markets and Holiday Lights
We arrived in Chicago early in the morning and made our way to the Chicago Athletic Association. Since our room wasn’t ready, we decided to take in the breathtaking views from Cindy’s, the hotel’s rooftop restaurant and bar. With sweeping vistas of Millennium Park and the Chicago skyline, it was the perfect way to kick off our trip.
Afterward, we headed down to the Game Room for lunch. This casual restaurant on the hotel’s 2nd floor serves pub-style food and offers fun activities like shuffleboard and billiards. The Game Room wasn’t a highlight but it helped by setting a relaxed tone for the afternoon.
Christkindlmarket: Chicago’s Best Christmas Market
After lunch, we headed over to Christkindlmarket at Daley Plaza, and wow—this place was the definition of holiday magic. Picture “city sidewalks, busy sidewalks,” emphasis on the BUSY part. Packed full of people soaking up the festive vibes.
This Christmas Market had it all: wooden stalls decked out with twinkling lights and garlands, the smell of roasted nuts and spiced cider in the air, and so much holiday cheer everywhere you looked.
People were wandering around with mugs of hot glühwein, checking out the handcrafted ornaments and other goodies. There were bratwursts, strudel, and just about every other festive treat you can think of. And chocolate… lots of chocolate.
It seriously felt like we’d stepped into a little slice of Europe.
Since we had a late lunch, we didn’t buy any food or drinks here. We were just at the Chritsmas Market to soak it all in. Honestly, walking around, people-watching, and seeing everyone enjoy themselves was half the fun.
Going to Europe for the Christmas markets (especially in Vienna and Prague) has been on our minds for a while, but this market turned out to be a fantastic substitute until next year.
Fresh off a girls’ trip to Montreal, Zuzu even said that Christkindlmarket was bigger and better than the best outdoor Christmas market she experienced there.
If you’re in Chicago for the holidays, you’ve got to check this place out. It’s not just a market—it’s like a holiday mood booster wrapped in twinkling lights.
Navy Pier: Lights on the Lake
That evening, we headed over to Navy Pier to check out the holiday light display, and it was seriously magical. The free exhibit stretched all the way down the pier, with sparkling lights and Christmas decorations everywhere you looked.
Bundling up in our coats and scarves made it all part of the experience. Walking along, we passed giant glowing ornaments, shimmering light tunnels, and so many picture-perfect spots.
Being right by the water added an extra vibe to it all. There’s just something about the lights reflecting off Lake Michigan with the city skyline behind you that makes everything feel a little more special.
Cheezborger, Cheezborger, Cheezborger!
To wrap up the day, we took Barry’s advice and had dinner at the Billy Goat Tavern.
This iconic dive bar, made famous by John Belushi in SNL’s “cheeseburger, cheeseburger” sketch, served up great cheeseburgers on the cheap. Trent loved it so much he said he’d probably go every week if he lived in Chicago.
Day 2 Itinerary: Sky-High Views and ZooLights
The day began with a phenomenal breakfast at the Cherry Circle Room. It was totally free as a perk of our Globalist status.
Free Breakfast at Cherry Circle Room
Kayla, our server, was wonderful!
Somehow, she convinced me to try a cheeseburger for breakfast. She said “I’m not passionate about much… but I’m passionate about this burger!”
It was fantastic and unlike any breakfast entrée I’d ever had!
When Trent was disappointed with the beverage options, Kayla made a special batch of lemonade just the way he wanted it. He loved it!
Millennium Park & The Bean
After breakfast, we headed across the street to Millennium Park, home to the iconic Cloud Gate sculpture, better known as “The Bean.”
It’s one of those landmarks you’ve seen a million times in pictures. But seeing it in person—especially during the holidays—was something else. We stopped to snap some photos, including one of the seasonal ice rink with The Bean glistening in the background.
As we smiled for this next picture, we noticed a commotion on the ice behind us but didn’t think much of it at the time. Later, we realized a skater had fallen and seriously hurt herself.
By the time the ambulance arrived, it was clear the situation was more serious than we’d first thought. Sandra quietly said, “That’s why I don’t skate anymore,” as we reflected on how quickly a fun moment can change.
We also counted our blessings that with all our travels, we’ve never gotten hurt on a trip. And we’ve been seriously ill only once, on a trip to Cancun.
Even with the unexpected turn of events, Millennium Park was still full of holiday energy. The rink was packed with skaters, the Chicago city Christmas tree stood tall, and the festive atmosphere was everywhere you looked.
94th Floor: 360 Chicago Observation Deck
In the afternoon, we visited the 360 Chicago Observation Deck in the John Hancock Building. The views from the 94th floor were nothing short of spectacular, showcasing the city’s skyline and Lake Michigan. Tickets were $35 each, and we spent an extra $10 for Trent to try the TILT experience.
TILT was kind of cool but didn’t really add much beyond the awe inspiring views that we got with the General Admission tickets. If you’re budget conscious like we are, you can skip TILT.
But overall, the 360 Chicago Observation Deck was our big splurge for the trip, and one of our favorite things to do on a Chicago trip.
Lincoln Park Christmas Lights
As evening fell, we used our CTA pass and hopped a bus to Lincoln Park for the ZooLights display. This holiday tradition features dazzling light installations throughout the zoo. Everywhere we turned, it was “beginning to look a lot like Christmas.”
Tickets were $7 per adult plus a small fee, making it an affordable and magical attraction. Despite the cold, we spotted several animals, including wolves, a red panda, and a polar bear. Rudolph did not make an appearance but we did see Père David’s deer.
Chicago Deep Dish Pizza
We ended the day with a late dinner at Pizano’s Pizza, trying Chicago’s famous deep-dish style. While the food was decent, we’ll try another pizza place next time and hope for better service.
Day 3: Departure
Room Service Breakfast, For Free!
Our final morning at Chicago Athletic Association began with breakfast via room service. Again, it was free thanks to our Globalist and Guest of Honor awards. The meal was fantastic, and the free breakfast benefit not only saves us money but often keeps our food costs down for the rest of the day.
After breakfast, the concierge arranged a private tour of the hotel for us, and it ended up being one of the highlights of our trip. Our guide walked us through the history of the Chicago Athletic Association, from its days as an elite men’s club in the 1890s to its transformation into a beautifully restored boutique hotel.
One of the most memorable stops on the tour was the ballroom, where the stunning stained glass windows offered an incredible view of The Bean in Millennium Park below.
The tour gave us a deeper appreciation for the hotel’s history, from its Venetian Gothic design inspired by the Doge’s Palace to the intricate craftsmanship throughout the building. Definitely a unique way to wrap up our stay before we packed up and took the Orange Line back to Midway Airport!
Midway Airport Lounge: Club MDW
At the airport, we stopped by the new lounge, where we saved money by enjoying their small buffet and free drinks.
The standout at Club MDW? Their chocolate chip cookies were as good as any specialty $5 cookie you’d find in an airport shop. It was the perfect way to end the trip with a sense of “having ourselves a merry little Christmas.”
Budget Breakdown
| Category | Cash Cost | Points Used | Cash Value |
|---|---|---|---|
| Flights | $166 | 23,148 SW pts | $300 |
| Hotel | $0 | 68,000 Hyatt pts | $1,621 |
| Transportation | $67 | – | $67 |
| Food | $196 | – | $196 |
| Entertainment | $138 | – | $138 |
| Total | $567 | 91,148 pts | $2,591 |
Using points and miles saved us over $2,000, making this holiday trip both affordable and luxurious.
Tips for Planning Your Chicago Holiday Itinerary
- Use Points and Miles: Booking flights and hotels with points can save thousands of dollars.
- Take Advantage of Public Transit: The CTA pass is a steal for unlimited rides.
- Visit Free or Low-Cost Attractions: Millennium Park, Navy Pier, and ZooLights offer fantastic experiences without breaking the bank.
- Dress Warmly: Chicago’s winter weather is no joke, so layers are a must.
- Consider All-Inclusive Resorts: lol, if you’d rather be on the beach than in the snow, check out our blog posts about our favorite all-inclusive resorts.
Chicago Holiday Trip, Worth it?
Our 2-day holiday trip to Chicago was packed with festive fun, family memories, and incredible value thanks to points and miles. Whether it’s ice skating at Millennium Park, exploring Christkindlmarket, or enjoying skyline views from 360 Chicago, this city has so much to offer during the holidays.
Ready to plan your Chicago holiday trip? Use this itinerary as a guide and start making memories! For more tips on maximizing points and miles, check out our other posts.
Looking for more ways to save on holiday trips? Don’t miss our free guide to (almost) free luxury travel, packed with tips to make every trip memorable and affordable.
Leave a Reply