Chicago, the Windy City, is the largest city in the Midwest. The Chicagoland tri-state area has a wide variety of museums, attractions and festivals — something to attract every type of traveler.

Here’s your points and miles guide to Chicago.

Getting to Chicago

Nearest airports

Figuring out how to get to Chicago with points and miles in 2021 starts with your flights. Chicago is served by two major airports:

O'Hare International Airport.

Chicago Midway International Airport.

Chicago-O'Hare is 18 miles northwest of downtown, while Chicago Midway is 12 miles to the southwest. Taxi fares vary depending on traffic conditions, but if you’re heading downtown, you can expect to pay $30 to $40 for a taxi from O'Hare and $35 to $45 from Midway. Ridesharing services are plentiful, and all major rental car companies are found at either airport.

For many people, the best way to get to downtown Chicago from either airport is via public transport. The Orange Line serves Midway with an approximate time of 25 minutes to downtown. The Blue Line serves O'Hare, and you can get to downtown in 45 to 60 minutes.

Major airlines flying to Chicago

There are three domestic airlines that have hubs or major operations in Chicago:

American Airlines (O'Hare).

United Airlines (O'Hare).

Southwest Airlines (Midway).

Because of Chicago’s large population, you’ll find flights there on most major airlines. In addition to Southwest, Allegiant and Delta also serve Midway, while most other airlines serve O'Hare, including Spirit, JetBlue, Frontier, Delta, American and Alaska.

Flying to Chicago on points and miles

With so many airlines headed here, you have plenty of options for how to travel to Chicago on points and miles. The number of miles you’ll need to fly American, United or Delta to Chicago will vary depending on the distance, route, date and time, among other factors.

Southwest Rapid Rewards

The points price for a Southwest flight is directly correlated to the flight's cash price. So when Southwest runs one of its frequent fare sales, this can often be a cheap and simple way to get to Chicago using points and miles. You can often find flights to Chicago Midway for around $50, especially if you live relatively close to Chicago.

Chase Ultimate Rewards®

Flexible points like Chase Ultimate Rewards® could be a good alternative to Southwest Rapid Rewards points. Ultimate Rewards® points prices are based on the cash price of the flight, but you can get a boost depending on which card you have. For example, Chase Sapphire Reserve® cardholders get 50% more value per point when they redeem points for flights through the Chase portal. With cash prices for flights so low, following this process step-by-step can often be the best points option for cheap flights to Chicago.

For example, a $99 fare deal would only cost only 6,600 Ultimate Rewards® points for a Chase Sapphire Reserve® card holder.

Other tips for flying to Chicago

Here are a few other tips if you are planning your Chicago trip with points and miles and flying or connecting through either of Chicago's two airports:

Navigating Chicago-O'Hare: Chicago-O'Hare has four terminals. Terminals 1, 2 and 3 are connected airside, making it easy to transfer between them. Terminal 5 is the international terminal, and transferring to it requires a shuttle bus (there is no active Terminal 4). Leave yourself plenty of time if you're making a domestic to international connection at O'Hare.

Navigating Chicago Midway: At Midway, all three terminals are connected airside, so it's quite easy to navigate between gates if you need to make a connection.

Lounges at Chicago-O'Hare: In the domestic terminals, United and American both have several of their standard lounges, and there is an American Flagship lounge and a United Polaris lounge. Delta also has a SkyClub in Terminal 2. In the international terminal, several international airlines have lounges. The only Priority Pass lounges are in the international terminal and not easily accessible to those flying domestically.

Lounges at Chicago Midway: Chicago Midway does not offer any airline or Priority Pass lounges.

Hotels on points in Chicago

There is a wide variety of hotels to book with points in Chicago. You can find budget hotels out by the airports or beyond, and many ultra-luxurious and iconic hotels downtown.

Chicago Hyatt hotels

Chicago has one of the densest collections of Hyatt hotels of any city in the world. No matter what your budget or desired location, you're likely to find a Chicago Hyatt that can fit your needs.

Park Hyatt Chicago

Photo courtesy of Hyatt

Chicago's Park Hyatt is located downtown on the Magnificent Mile.

Cost to book in points: Rooms at this Category 6 World of Hyatt property start at 21,000 points per night for off-peak bookings. NerdWallet values Hyatt points at 2.3 cents per point. There are no resort fees, but you'll be charged $74 for overnight parking.

Hyatt Regency Schaumburg, Chicago

The Hyatt Regency Schaumburg, Chicago is one of nearly a dozen Category 1 World of Hyatt hotels in the Chicago area, meaning your points will go far here.

Cost to book in points: Category 1 rooms start at 3,500 points per night for off-peak dates. There are no parking or resort fees at the Hyatt Regency Schaumburg.

How to earn Hyatt points: The World of Hyatt Credit Card is one of the better hotel credit cards and also offers a path to elite status through spending. World of Hyatt is a Chase transfer partner, so if you have Chase Ultimate Rewards® points, you can transfer them to World of Hyatt at a 1:1 ratio.

Chicago Marriott hotels

Marriott also has a wide variety of hotels throughout Chicago, with over 20 hotels just in the downtown/Magnificent Mile area.

Ritz-Carlton Chicago

The Ritz-Carlton Chicago is located in Chicago's Gold Coast, just north of downtown.

Cost to book in points: Rooms can start as low as 43,000 points per night, but rates will vary based on demand. NerdWallet values Marriott Bonvoy points at 0.8 cent per point. There are no resort fees charged on award or paid stays.

How to earn Marriott Bonvoy points: One way to earn Marriott Bonvoy points is the Marriott Bonvoy Brilliant® American Express® Card. One of the card’s benefits is the complimentary free award night, valued up to 85,000 points. Terms apply.

If you want status in the Marriott Bonvoy program, but you don’t want to commit to a Marriott Bonvoy-branded credit card, consider The Platinum Card® from American Express, which comes with automatic Marriott Gold Status. Plus, the card is currently offering a welcome bonus: Earn 80,000 Membership Rewards® Points after you spend $8,000 on purchases on your new Card in your first 6 months of Card Membership. Those points can typically be transferred to the Bonvoy program at a 1:1 ratio.

Chicago Hilton hotels

Hilton also has a wide variety of hotels throughout Chicagoland. No matter where you're looking to stay or how many points you want to spend, you'll have a hotel that fits your needs.

Palmer House, a Hilton Hotel

Built in 1871 at the corner of State and Monroe, the historic Palmer House is one of the most iconic hotels in downtown Chicago.

Cost to book in points: Expect to spend between 30,000 and 50,000 Hilton Honors points per night for a standard room. NerdWallet values Hilton points at 0.4 cent per point. There are no resort fees, but you’ll pay $52 a day for self-parking or $82 for valet parking.

How to earn Hilton Honors points: The Hilton Honors American Express Surpass® Card gives you an opportunity to earn a free night by spending $15,000 on the card in a year. It will also get you automatic Gold status in the Bonvoy program. The Hilton Honors American Express Aspire Card comes with an automatic free night, plus automatic Diamond status. Terms apply.

If you want Hilton Honors Gold status, but don’t want to commit to a Hilton-branded credit card, consider The Platinum Card® from American Express, which also comes with automatic Hilton Gold Status.

Membership Rewards points can be transferred to the Hilton Honors program at a 1:2 ratio, which means 1 American Express Membership Rewards point can be turned into 2 Hilton points.

You can use miles and points to book an affordable Chicago trip

Chicago is a world-class city that is accessible with points and miles. For a more luxurious experience, stay downtown at the center of everything. If you're looking to save even more money, consider staying in the suburbs and taking public transit into downtown. If you're driving to Chicago or renting a car, make sure you're aware of the hefty parking fees at downtown hotels.

All information about the Hilton Honors American Express Aspire Card has been collected independently by NerdWallet. The Hilton Honors American Express Aspire Card is no longer available through NerdWallet.

To view rates and fees of The Platinum Card® from American Express, see this page.