Chicago does the holidays big. The Christkindlmarket fills Daley Plaza, Michigan Avenue gets its parade and fireworks, and the zoo turns into a light show. For Midwest travelers it is also one of the easiest holiday trips to book on points: two big airports, a short train ride from Milwaukee, and award hotels from every major chain within walking distance of the action. Here is what is confirmed for 2026 and where we would look to stay on points.
Chicago holiday events for 2026 (as of October 2026)
Every date below comes from the organizer or the city, cross-checked with local news where we could. Hours can change, so check the event’s own page before you go.
| Event | 2026 dates | Hours and cost |
|---|---|---|
| Christkindlmarket, Daley Plaza (50 W. Washington St.) | Daily, Nov. 20 to Dec. 24 | Sun. to Thu. 11 a.m. to 8 p.m.; Fri. and Sat. 11 a.m. to 9 p.m.; Thanksgiving (Nov. 26) and Christmas Eve 11 a.m. to 4 p.m. Free admission. |
| Christkindlmarket, Wrigleyville (Gallagher Way, 3635 N. Clark St.) | Daily, Nov. 20 to Dec. 31 (closed Dec. 25) | Mon. to Thu. 3 to 9 p.m.; Fri. and Sat. 11 a.m. to 9 p.m.; Sun. 11 a.m. to 7 p.m.; extended hours some holiday weekdays. Free admission. |
| Christkindlmarket, Aurora (RiverEdge Park) | Thu. to Sun., Nov. 20 to Dec. 24, plus some extra weekdays | Hours vary by day. Free admission. |
| City of Chicago Christmas Tree Lighting, Millennium Park | Friday, Nov. 20 | Ceremony starts at 6 p.m. |
| Wintrust Magnificent Mile Lights Festival | Saturday, Nov. 21 | Lights Festival Lane at Pioneer Court 11 a.m. to 4 p.m.; parade 5:30 p.m. from Oak Street south on Michigan Avenue; fireworks around 7:15 p.m. Free. |
| Lincoln Park ZooLights | Nov. 20, 2026 to Jan. 3, 2027 | 4:30 to 9 p.m. (last entry 8 p.m.). Fixed-date tickets $7 to $12 in advance, $20 day-of or flexible; free Mondays with a reservation (Nov. 23, Nov. 30, Dec. 7, Dec. 14). Closed Nov. 26, Dec. 1, 8, 15, 24 and 25. |
Notice the pattern: the markets, the tree lighting and ZooLights all start on Friday, November 20, and the Lights Festival parade is the next day. That makes November 20 to 22 the most exciting weekend of the season and probably the most crowded and expensive one for hotels. If you would rather browse the market without the crush, a weekday in early December is a calmer bet.
For other cities’ markets, see our roundup of the top Christmas markets for 2026.
Getting to Chicago on points and miles
- O’Hare (ORD) is a hub for both United and American, so it is the natural pick for MileagePlus and AAdvantage awards. The CTA Blue Line runs 24 hours a day and takes about 40 to 45 minutes to downtown.
- Midway (MDW) is a major Southwest base, which makes it the Rapid Rewards option. The CTA Orange Line reaches the Loop in about 20 to 25 minutes, though it does not run overnight.
- From Milwaukee, Amtrak’s Hiawatha runs to Chicago Union Station in about an hour and a half, with multiple round trips a day. For a holiday weekend that can beat flying.
Where to stay downtown on points
Marriott, Hilton and IHG all price award nights dynamically, so the points cost moves with the cash rate and holiday weekends can price high. Search your exact dates on each chain’s site or app, and book a refundable award so you can rebook if the price drops.
Park Hyatt Chicago (World of Hyatt)
On Michigan Avenue near the historic Water Tower, the Park Hyatt is a short walk from the Magnificent Mile parade route. It has a pool and the NoMI Kitchen restaurant. Points guides list it as a Category 6 hotel. Under the award chart Hyatt introduced on May 20, 2026, a standard room at a Category 6 hotel costs between 20,000 and 40,000 points a night depending on the date (five price levels, from “Lowest” to “Top”). That is often excellent value next to paid December rates, and Chase Ultimate Rewards points transfer to Hyatt. Confirm the hotel’s current category and your dates on hyatt.com.
JW Marriott Chicago (Marriott Bonvoy)
Set in a 1914 Daniel Burnham-designed former bank at 151 W. Adams St. in the Loop, the JW Marriott is a good base for the Daley Plaza market. It has an indoor heated pool, a spa and an executive lounge for qualifying Bonvoy elites. If you prefer a lakefront tower, our Christmas markets guide covers the St. Regis Chicago, another Bonvoy option.
Palmer House, a Hilton Hotel (Hilton Honors)
At 17 E. Monroe St., the Palmer House is about two blocks from the Art Institute and Millennium Park. It opened in 1871, calls itself the longest continuously operating hotel in North America, and is known for its original Palmer House brownie. With more than 1,600 rooms, it is a Hilton option that is often worth checking when smaller hotels sell out.
InterContinental Chicago Magnificent Mile (IHG One Rewards)
At 505 N. Michigan Ave., the InterContinental sits on the stretch of Michigan Avenue the Lights Festival parade travels. Its indoor junior Olympic-size pool, with 1920s tilework, is a nice break on a cold afternoon (note that IHG says the pool area is not wheelchair accessible).
Practical tips
- Book early, cancel freely. Lock in a refundable award night now for the November 20 weekend or a December Saturday, then keep checking prices.
- Mind the short days. Daley Plaza closes at 4 p.m. on Thanksgiving and Christmas Eve, and Wrigleyville does not open until 3 p.m. Monday to Thursday.
- Pick ZooLights tickets carefully. Fixed-date tickets are cheapest but cannot be changed or transferred. Free Monday reservations open one week ahead at 11 a.m. CT.
- Skip the car. Downtown hotel parking is expensive, and the CTA connects both airports with the Loop.
- Dress for wind. Most of these events are outdoors along the river and the lake.
Chase Ultimate Rewards points transfer to World of Hyatt, United and Southwest, which covers the Park Hyatt and both Chicago airports. You can compare current offers and apply with our Chase referral link.
Disclosure: This is our personal Chase referral link. If you’re approved through it, we may earn a referral bonus, at no extra cost to you. You can always apply directly on Chase’s website. See our Advertising & Referral Disclosure.
Our take
If you want one holiday city weekend in the Midwest, Chicago is hard to beat, and the Park Hyatt is the standout points play if your dates price at the lower Hyatt levels. The downsides are real, though: opening weekend will be packed, dynamic pricing at Marriott, Hilton and IHG can make December Saturdays expensive in points, and the weather can be brutal. Go midweek if you can, book refundable, and keep a backup hotel in mind.
Sources
- Christkindlmarket Chicago: Daley Plaza
- Christkindlmarket: Wrigleyville
- CBS Chicago: Christkindlmarket returning to Daley Plaza in 2026
- Wintrust: Magnificent Mile Lights Festival 2026
- ABC7 Chicago: 2026 Christmas tree lighting
- Chicago Sun-Times: Search underway for Chicago’s next Christmas tree
- Lincoln Park Zoo: ZooLights
- CTA: Airports
- Amtrak: Hiawatha
- Park Hyatt Chicago
- Upgraded Points: World of Hyatt category and chart changes, May 2026
- The Points Guy: Hyatt’s new award charts
- Platinum Flyer: Chicago on points
- JW Marriott Chicago
- Palmer House, a Hilton Hotel
- InterContinental Chicago Magnificent Mile
Prices, points rates, schedules and entry rules change often; confirm details with the airline, hotel or organizer before you book. Points Capital is not a financial advisor.
