Weekend Getaways: Chicago

A true gem along the shores of Lake Michigan, Chicago is a Midwestern icon that shouldn’t be missed. If you don’t have a ton of time to spare, a weekend getaway to the Windy City is the perfect amount of time to hit the highlights, enjoy some great eats and make your way down Michigan Avenue for unbeatable shopping.

No matter how you plan to get there or where you plan to stay, we can help you book with confidence using your points and miles. Read on to discover our recommendations for an unforgettable weekend in Chicago complete with sample itineraries, accommodation options, places to go and where to eat.

How to Book Flights to Chicago on Points and Miles

When flying to Chicago, your best bets of the Big Three are United Airlines and American Airlines. Chicago O’Hare (ORD) is a major hub for these two airlines, but if you’re searching for budget options, Frontier Airlines and Spirit Airlines also feature plenty of routes in and out of Chicago. Southwest Airlines has a hub at Chicago-Midway (MDW), which is another great option.

United Airlines

United offers a wealth of options including flights from Denver (DEN); New York-La Guardia (LGA); Portland, Oregon (PDX); Boston (BOS); Fort Lauderdale, Florida (FLL); and many other airports across the U.S.

Nonstop one-way flights between Fort Lauderdale and Chicago are often cheap and start from just 5,000 MileagePlus miles, but because the award calendar is based on a dynamic pricing model, flip through the calendar to find the cheapest available dates that suit your schedule.

American Airlines

Like United, American Airlines offers quite a few direct routes across the U.S. because Chicago O’Hare is one of its hub airports. Direct routes include San Francisco (SFO); Austin, Texas (AUS); New York (LGA, EWR and JFK); Miami (MIA); and many more.

One-way flights between Chicago and New York-JFK are on offer from just 6,000 AAdvantage miles, but since American Airlines also uses a dynamic pricing model, you’ll have to check the redemption rate for your preferred dates.

Another option is to book with Avios through British Airways because its awards chart isn’t dynamic but rather distance-based—you might find a better deal there.

Frontier Airlines and Spirit Airlines

If you’d prefer to fly on a low-cost carrier with points and miles, we recommend booking through the Chase Ultimate Rewards travel portal. This is because the cheap cash value isn’t always worth the brand-specific points redemption, and points redeemed for travel are worth more through Ultimate Rewards. Depending on your home airport, redeeming Ultimate Rewards points on a Frontier or Spirit itinerary could be your cheapest option.

Southwest Airlines

Those who are OK with flying into Chicago-Midway should consider Southwest flight options. Southwest also offers select flights into Chicago O’Hare, which started in 2021.

Southwest prices awards based on cash fares, so you won’t be able to find incredible value for your Southwest Rapid Rewards points. However, it’s possible to find low-priced redemptions starting from just 2,500 Rapid Rewards points each way.

Where to Stay in Chicago with Points and Miles

Budget Options

Budget options run the gamut between “As cheap as possible” and “Wait, this is an incredible deal!” We’ve selected one of each for your consideration.

For the “cheap as possible” option, the Chicago Getaway Hostel offers a trendy locale in the heart of Lincoln Park. While hostels are great for those who like the social aspect of travel, you have the possibility to book private accommodations here as well as shared accommodation.

A night at Chicago Getaway will put you back $63 or just 4,200 Chase Ultimate Rewards points if you have the Chase Sapphire Reserve® and can redeem your Ultimate Rewards points at a value of 1.5 cents per point.

On the other end of the spectrum, you would think that a $200+-per-night hotel wouldn’t belong in the budget section. But when booked with just 12,000 World of Hyatt points, the Chicago Athletic Association – In the Unbound Collection by Hyatt becomes a great budget choice. Hyatt tends to collect reimagined buildings with deep historical roots, and this property is no exception. The Chicago Athletic Association is tucked inside a Venetian Gothic 1893 building located just across the street from Millennium Park.

If we had to pick between the two, we’d choose the Chicago Athletic Association for its history and design. They both seem like cool places to hang out, but for just 12,000 World of Hyatt points, the Chicago Athletic Association comes out on top for us.

Mid-Range Options

In Chicago, it’s no problem finding a mid-range option in the heart of downtown. Many of these properties are repurposed historical buildings, two of which we have highlighted for you below.

Formerly the London Guarantee & Accident headquarters, the LondonHouse Chicago, Curio Collection by Hilton, still stands proudly above the Chicago River and features incredible views of the riverside skyline.

You can snag a night for 65,000 Hilton Honors points, or $130 per night, but you can pick up a night here from just 8,666 Chase Ultimate Rewards points if you have the Chase Sapphire Reserve® when the cash price is that low.

While the two point systems scale a lot differently, this is a total steal through the Ultimate Rewards portal. When you’ve decided on an ideal hotel, it’s always a good idea to compare cash prices with award rates for booking directly through the hotel program and then consider whether you have flexible points that can be used to book the hotel at a more favorable rate.

Another neat mid-range option is The Publishing House Bed & Breakfast, a trendy combination that blends the comfort of a B&B with the style of a boutique hotel. Formerly the Free Methodist Publishing house, this property is located in the desirable West Loop neighborhood. The cash value for a night is $195, but we recommend redeeming just 13,000 Chase Ultimate Rewards points instead for those who have the Sapphire Reserve.

For us, The Publishing House is just too neat of a concept to pass up. Plus, the redemption through the Ultimate Rewards portal is always a solid use of points because you know you’re getting 1.25 to 1.5 cents per point in value depending on which Chase Ultimate Rewards-earning card you have.

Luxury Options

Luxury is relative, and Chicago has plenty of options to suit whatever luxury means to you. While these two properties are wildly different in price, they fall under the luxury category in their own different ways.

Hailing from Marriott’s luxury brand, The Gwen, a Luxury Collection Hotel, brings art and design into every detail. Each room features a custom mural by Gwen Lux, the artist after whom the hotel is named.

This Category 6 property is available from $197 or 40,000 Marriott Bonvoy points per night, so if your dates are flexible, search for an off-peak time of year for the best deal and always compare the points and cash prices to make sure you’re getting good value for your points. We recommend looking for redemptions where a Bonvoy point is worth at least 0.5 cent, but even better to get into the 0.8 to 1 cent per point rate.

One of Chicago’s favorite five-star hotels, The Peninsula is available to book through the Ultimate Rewards portal, where the 31,666-point redemption will offset the $475-per-night cash price if you have the Chase Sapphire Reserve®. The Peninsula highlights its expertly crafted mix of “Far Eastern graciousness and Midwestern hospitality,” a winning combination for those looking for a comfortable and elegant stay.

If we had to pick, we’d recommend The Peninsula. It’s a great way to redeem a stash of Ultimate Rewards points and avoid a hefty nightly rate, plus the cultural combination is an enticing and unique concept.

Things to Do in Chicago

There is never a shortage of things to do in Chicago, especially for folks who enjoy being outdoors, exploring urban green spaces, strolling through museums, learning new things or catching a baseball game.

Wrigley Field

Whether you’re a die-hard MLB fan or just in town for the Chicago-style dogs, catching a game at Wrigley Field is a must. When it isn’t game day, Wrigley Field offers tours of the ballpark for curious Cubs fans. Be sure to check the schedule beforehand and download the MLB Ballpark app to access your mobile ticket.

Shedd Aquarium

For lifelong learners and lovers of the sea, Shedd Aquarium is a great daytime activity. Learn about the strange inhabitants of our underwater worlds including beluga whales, sharks and giant octopi. You will need to purchase a ticket for a specified time in advance and note that you must be fully vaccinated against COVID-19 to visit Shedd Aquarium.

Art Institute of Chicago

Featuring exhibits that span space and time, a visit to the Art Institute of Chicago could occupy your entire weekend. Don’t miss the temporary exhibitions such as Senju’s Waterfall for Chicago, the Golden Age of Kabuki Prints and Ray Johnson ℅. The permanent collection onsite is also worth seeing again and again, including works by Vincent van Gogh, Georgia O’Keefe and Diego Rivera.

Adler Planetarium

If you’d like to reconnect with your inner child, lean back and watch the stars, then we highly recommend a visit to Adler Planetarium for a sky show. Plan ahead and explore Adler’s many exhibits, including Chicago’s Night Sky, Astronomy in Culture, Mission Moon and the historic Atwood Sphere.

Navy Pier

There are few things nicer than taking a stroll down Navy Pier on a sunny day, enjoying the fresh Lake Michigan air and a nice ice cream cone. Not only does Navy Pier have a wealth of dining and shopping options along the way, but it also features a full schedule of free public events. Check the calendar beforehand, aim for the Ferris wheel and enjoy taking your time along the pier. Additionally, you can book sunset cruises from Navy Pier that are perfect for a warm night.

Favorite Food and Drink Stops

Eats

• The Purple Pig: An iconic gastropub perfect for big fans of “cheese swine and wine.”
• Ed Debevic’s: Chaos and sass rule at this ’50s diner with a snarky wait staff, plenty of dropped trays and impromptu dance numbers.
• Jim’s Original: A Polish sausage stand with more than 80 years of delicious history.

Drinks

• Revolution Brewing: A must-stop for lovers of local brews.
• The Drunken Bean Coffee & Wine Bar: A great brunch spot for those who can’t decide between a steaming cappuccino or a sparkling mimosa.
• The Matchbox: An intimate, iconic neighborhood bar founded in 1945.
• Sawada Coffee: The first U.S. cafe of latte artist Hiroshi Sawada, featuring ping-pong and a punching bag.

How to Earn Points

Your best bet for the aforementioned redemptions is definitely the Chase Sapphire collection, specifically the Chase Sapphire Reserve® or the Chase Sapphire Preferred® Card. Since Chase Ultimate Rewards points are transferable between Chase’s airline partners, you’d be able to repurpose your points on flights to Chicago on American Airlines (with British Airways Avios), United Airlines and Southwest Airlines.

In addition, Marriott and Hyatt are both hotel partners of Chase. This means that you could transfer your Ultimate Rewards points for a stay at the Chicago Athletic Association or The Gwen. However, we don’t recommend transferring Chase Ultimate Rewards points to Marriott Bonvoy as it typically doesn’t offer redemptions that are as high of value.

As mentioned before, you can redeem Ultimate Rewards points on a stay at Hilton’s LondonHouse Chicago, but Hilton is not a transfer partner, so you’d have to book directly through the Ultimate Rewards portal.

You can use your Chase Ultimate Rewards to book any hotel in Chicago that’s available through the Chase Ultimate Rewards portal, where your points are worth 1.25 to 1.5 cents each, depending on which Chase Ultimate Rewards-earning card you have.

Speaking of Hilton, you may consider investing in a Hilton credit card. With four cards currently available, offering some hefty welcome bonuses, you could get at least a free two-night stay by qualifying for one of those. The Hilton card options include:

• Hilton Honors American Express Aspire Card
• Hilton Honors American Express Surpass® Card
• Hilton Honors American Express Card
• The Hilton Honors American Express Business Card

The World of Hyatt Credit Card comes with a tiered bonus.

The Marriott Bonvoy Boundless® Credit Card welcome bonus varies, sometimes the bonus comes in the form of points and sometimes in the form of free night certificates. Other Marriott cards to consider include:

• Marriott Bonvoy American Express Card
• Marriott Bonvoy Brilliant® American Express® Card
• Marriott Bonvoy Business® American Express® Card
• Marriott Bonvoy Bold® Credit Card

The most versatile suite of cards, though, is still the Chase Sapphire collection. You can either transfer points or redeem them for all of the aforementioned flights and properties, making it one of the most valuable currencies in the industry.

Final Thoughts

Whether it’s art, shopping, dining or exploring, Chicago has something to suit everyone. Chicago is a massive airline hub, culture center and vibrant metropolis with options galore for your points and miles redemptions. Now, your most difficult decision is deciding when to visit.

Although winter in the Windy City can be rough, we’ve mentioned plenty of indoor activities in case you just can’t wait until warmer weather. Otherwise, the best times to visit are late spring and early autumn—these times get you away from the scorching summer and crowds, but they’re also far from the plunging temperatures of “Chiberia.”

No matter when you visit Chicago, you’ll have plenty of opportunities to make memories that last a lifetime.