Your Points and Miles Guide to Chicago

Update: Some offers mentioned below are no longer available. View the current offers here – Starwood Preferred Guest® Credit Card from American Express, Southwest Rapid Rewards Premier Credit Card, Chase Sapphire Preferred Card

In the latest installment of our "Points and Miles Destination Guide" series, TPG Contributor Whitney Magnuson explores the many different ways to maximize a trip to Chicago using points and miles.

Chicago is one of my favorite cities in the country. Full of friendly people, fantastic restaurants and wonderful museums, this "Jewel of the Midwest" is a great place to spend some downtime. And I'm not alone in that opinion — more than 7 million passengers make their way through Chicago's O'Hare airport each month, as the destination is popular among both business and leisure travelers, in addition to being a common jumping-off point for international travel. Below, I'll outline several strategies for using miles and points to plan a trip to the Windy City.

Getting There

Chicago has two large airports: Chicago O'Hare International (ORD), which services the majority of traffic through the city, as well Chicago Midway International (MDW), which almost exclusively handles Southwest flights.

All three of the US majors — American, United, and Delta — fly through O'Hare, with Delta offering very limited service to Midway as well. American and United both offer zone-based awards, meaning you'll pay the same number of points from any American origin city, even if you can't fly nonstop. Saver Awards on United and MileSAAver Awards on American will both run you 12,500 miles in economy or 25,000 miles in business/first in a two-cabin aircraft.

Because Chicago is located in the middle of the country, a wealth of other North American cities quality for the award sweet spot accessible by booking American Airlines awards using British Airways Avios. Cities within 650 miles of Chicago — including Atlanta, Cleveland, Detroit, Indianapolis, Kansas City, Minneapolis, Nashville, Toronto and Washington, D.C. — qualify as Zone 1 awards, requiring just 4,500 Avios each way. Albuquerque, Austin, Dallas, Denver, Montreal, New York and Philadelphia fall within Zone 2, requiring a still reasonable 7,500 Avios. Even better, these flights won't get hit with the notoriously steep fuel surcharges common on British Airways.

Meanwhile, both Delta and Southwest now base their award flights in part on the cash price of the ticket; the number of miles required for a ticket therefore varies widely depending on departure city. Southwest recently increased the bonus available on the Southwest Rapid Rewards Premier Credit Card to 40,000 points (after spending $1,000 within the first three months), putting the Southwest Companion pass once again within reach. With a Companion Pass, even the revenue-based award chart can work out to a good deal if you're traveling as part of a twosome.

Virgin America is another option for West Coast travelers. Daily nonstops to Chicago from Los Angeles and San Francisco go for as low as $119 or 4,837 Elevate points, while first class is available for as little as $377 or 16,837 points. Note that you can transfer American Express Membership Rewards to Virgin America at a 2:1 ratio.

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Finally, there are plenty of international routes that fly nonstop to Chicago. Etihad flights to and from Abu Dhabi can be had at a good value using AAdvantage points, though it's worth noting they use the older 777-300s on the route, not the newer A380s featuring The Residence. You can also redeem American miles for Cathay Pacific's nonstop flight to/from Hong Kong — the carrier's first class is one of TPG's favorite products to fly to or from Asia.

Where to Stay

There's a lot to see and do in Chi-town, and a great hotel in the center of the action can help make your stay even better. Starwood has several properties within the city center, many of which offer good redemption values. The W Chicago City Center, a Category 5 property, offers the brand's signature modern amenities for nightly rates starting at about $360 or 12,00 points per night, which works out to 3 cents per point in value — favorable given TPG's latest valuations, which peg Starpoints at 2.5 cents apiece.

Another good redemption option is The Gwen, a property within the Starwood Luxury Collection that just debuted this month. Located in the historic McGraw Hill building, The Gwen feature spacious guest rooms and a rooftop bar, with rooms starting at about $310 a night. At this Category 5 hotel, free nights costs 12,000 points, translating to a redemption value of 2.6 cents per point. If you don't mind parting with some cash for a better redemption rate, check out the hotel's cash + points option for multiple dates through the fall, where a room costs 6,000 points plus $110.

Considering the up to 25,000-point bonus currently offered on the Starwood Preferred Guest Credit Card from American Express for spending $3,000 within the first three months of card issue, a one-night stay at either hotel is easily within reach.

Hyatt loyalists are also well covered in the Second City. Convention attendees in particular should check out the Hyatt Regency McCormick Place, which is just minutes from the Convention Center steps. For just 12,000 points or roughly $270 a night, it's usually a better redemption option than the Hyatt Regency Chicago, which is located closer to Navy Pier.

As Chase Ultimate Rewards points transfer 1:1 to Hyatt, a traveler hoping to nab a free night at either hotel might consider the Chase Sapphire Preferred Card. By spending $4,000 in the first three months and adding an authorized card holder, you'll earn 50,000 UR points — enough for a three-night stay.

If you're seeking a bit of luxury on your Chicago trip, Marriott's options are worth a look. Located just a few blocks from the Willis Tower, the JW Marriott Chicago welcomes guests with a lobby full of crystal chandeliers. Rooms average about $400 a night, or can be redeemed for 40,000 points per night.

A room at the Ritz-Carlton Chicago is also a possibility with Marriott points; as a Tier 3 property, it requires 50,000 points per night. Note that award nightss are limited in quantity, and availability is already pretty spotty through the end of the year.

One thing to keep in mind with Marriott redemptions is that the brand offers a fifth night free on award stays, which essentially equates to a 20% bonus in value. For example, a five-night stay at the JW Marriott Chicago would require $2,000, but only 160,000 Marriott points, thereby upping the redemption value to 1.25 cents per point.

Wyndham's offerings are also worth considering. Since the chain went to a flat-rate redemption model of 15,000 points per night, stays at higher-end properties can be a great deal. The Wyndham Grand Chicago Riverfront offers rooms for about $300 a night, and has great "go-free" award availability through the rest of the year. Considering the Wyndham Rewards Visa Card comes with a bonus offer of 30,000 points (15,000 after your first purchase, and 15,000 more after you spend $1,000 within the first 90 days), a two-night stay at the four-star property is attainable with a single card bonus.

Finally, if Chicago is just a temporary stop and/or you have an early morning flight, you may want to check in to a hotel near the airport. The Sheraton Chicago O'Hare Airport Hotel runs travelers $224 a night, but offers free nights for just 7,000 points, for a redemption rate of 3.2 cents per point. Meanwhile, the Hyatt Rosemont offers contemporary rooms and a free hotel shuttle for just $189 or 8,000 Hyatt points per night, for a redemption rate of about 2.4 cents per point.

Getting Around

Once you make it to Chicago, you can either look for ground transport — a bevy of taxis, Ubers and Lyfts will greet you just outside the terminal — or board the iconic "L" train (also known as the Blue Line), which stops at the O'Hare terminal at least four times an hour. And if you've already made it into town and are looking for something to do, I'd highly recommend the Chicago architecture river cruise for a completely different perspective on all those tall buildings.

However you get there, enjoy your stay in the Windy City, and check out these other TPG articles to help plan your trip:

• Layover Lowdown: Chicago O'Hare International Airport
• 8 Chicago Restaurant Hot Spots for Every Occasion
• A Week in the Admirals Club: Chicago O'Hare International Airport
• 2015 Chicago Seminar Tickets Now On Sale

What are your favorite tips for using points and miles for a trip to Chicago?