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Lollapalooza is happening — here's how to use your points for flights and hotels

Andrew Kunesh
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Andrew Kunesh is a former senior editor at The Points Guy covering loyalty programs. He's been a miles and points fanatic since 2014 and previously wrote for Upgraded Points and Credit Karma. Outside of the travel world, Andrew is a cyclist, craft coffee aficionado and — despite now living in NYC — a Chicagoan at heart.
May 21, 2021
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17 min read
Saba performing at Lollapalooza Chicago in 2019
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Lollapalooza — Chicago's largest music festival — is back after 2020's event was canceled due to the coronavirus pandemic. The event takes place from July 29 to August 1, and headliners include huge names like Foo Fighters, Post Malone and Miley Cyrus. You must be vaccinated against COVID-19 or bring a negative COVID test that's less than 24 hours old to attend.

Interested in attending but don't want to break the bank on travel? Your points and miles can help. Here, I'll show you the cheapest award flights and best nearby points hotels you can book to lower the cost of your trip.

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Cheapest award flights to Chicago

United's largest hub is at Chicago-O'Hare (ORD). (Photo by EQRoy/Shutterstock)

Chicago has two airports: Chicago-O'Hare (ORD) and Chicago-Midway (MDW). O'Hare, the larger of the two, is a hub for American and United and serviced by all major airlines. Midway is a "hub" for Southwest Airlines (though the airline now flies to O'Hare too) and is also served by Delta and a handful of low-cost carriers.

Here's how to use your points and miles to book award tickets to Chicago for Lollapalooza.

Related: The 5 best domestic award chart sweet spots

Book Star Alliance award tickets with Turkish Airlines Miles & Smiles

Your best bet for booking United awards is Turkish Airlines Miles & Smiles. This program charges just 7,500 miles one-way anywhere within the U.S. — even long-haul flights from Hawaii. Plus, business class costs just 12,500 miles one-way. This is one of the best deals out there for domestic award flights.

(Screenshot courtesy of Turkish Airlines)

You can transfer Capital One, Citi ThankYou and Marriott Bonvoy points to Turkish Airlines. The Capital One Venture Rewards Credit Card currently offers 75,000 bonus miles when you spend $4,000 on purchases in the first three months from account opening.

Related: 9 things no one tells you about… Chicago

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Book Oneworld award tickets with British Airways Avios

Alternatively, you can book American and Alaska flights with British Airways Avios. Because of the airline's distance-based award chart, the price you'll pay depends on how long your flight is. Flights within North America start at 7,500 Avios one-way for flights up that are up to 1,151 miles long. This is a great way to use Avios without spending a lot on fuel surcharges.

(Screenshot courtesy of British Airways)

You can transfer American Express Membership Rewards, Capital One, Chase Ultimate Rewards and Marriott Bonvoy points to Avios. Consider opening one of these Chase cards to earn points for your ticket:

  • Chase Sapphire Preferred Card – Earn 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.
  • Ink Business Preferred Credit Card – Earn 100,000 bonus points after you spend $15,000 on purchases in the first three months from account opening.
  • Chase Sapphire Reserve – Earn 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.

Related: 7 things to do in Chicago with kids

Book SkyTeam award tickets with Delta SkyMiles

Finally, Delta frequently offers low-cost SkyMiles award tickets to Chicago. You can fly to Chicago from most of the airline's hubs, sometimes for as little as 4,500 SkyMiles one-way. Prices vary daily since Delta now prices all award tickets dynamically.

(Screenshot courtesy of Delta)

American Express and Marriott points transfer to Delta, or you can earn with one of the carrier's many cobranded credit cards. Here's a look at the best American Express card offers:

  • American Express® Green Card: Earn 60,000 Membership Rewards points after you spend $3,000 on purchases within the first six months of card membership. Plus, 20% back on eligible travel and transit purchases in the first six months, up to $200 back in the form of a statement credit. Earn 3x points on dining at restaurants, travel and transit (including flights, hotels, taxis, tours, and ridesharing services), 1x points on all other purchases ($150 annual fee; see rates and fees).
  • American Express® Gold Card: Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new card within the first six months of account opening. Earn 4x points on dining at restaurants; 4x points at U.S. supermarkets (up to $25,000 per calendar year; then 1x points); 3x points on airfare purchased directly from airlines or American Express Travel; 1x points on all other purchases, ($250 annual fee; see rates and fees).
  • The Platinum Card® from American Express: Earn 80,000 Membership Rewards Points after you spend $6,000 on purchases within the first six months of card membership. Earn 5x points on airfare purchased directly from airlines or with American Express Travel (earn 5x points on up to $500,000 on these purchases per calendar year), 5x on prepaid hotels booked with American Express Travel, and Amex Fine Hotels & Resorts; 1x on all other purchases, ($695 annual fee; see rates and fees).

Related: Book this, not that: SkyTeam award tickets

Points hotels near Lollapalooza

Lollapalooza is in Grant Park, which is right in the middle of downtown Chicago (aka "the Loop"). There are several hotels across all the major hotel chains, so it's easy to use your points to book a few nights for the festival without paying out of pocket. You'll want to book your hotel soon, since they fill up quickly during Lollapalooza.

Here's a look at your best points hotel options near Grant Park.

Related: Use points at these 9 family-friendly Chicago hotels

Hilton hotels near Lollapalooza

Use your Hilton Honors points to stay at the Palmer House, one of the oldest hotels in Chicago. (Photo by Nagel Photography / Shutterstock.com)

Hilton has a large footprint in Chicago, with many hotels located right near Grant Park. The closest hotel is the Hilton Chicago, which is just across the street from the festival. Here's a look at all your options — just remember that Hilton Honors has dynamic pricing, so the prices listed are for the first night of Lollapalooza.

  • Hilton Chicago: 59,000 points per night
  • Hilton Garden Inn Chicago Downtown Riverwalk: 60,000 points per night
  • LondonHouse Chicago: 67,000 points per night
  • Palmer House: 60,000 points per night
  • theWit Chicago: 70,000 points per night

You can earn Hilton Honors points with one of these Hilton cobranded credit cards. Each has a different set of benefits, like complimentary elite status and free night certificates.

The information for the Hilton Aspire Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Related: How to redeem points with the Hilton Honors program

Hyatt hotels near Lollapalooza

The Chicago Athletic Association has multiple on-site restaurants, including a Shake Shack. (Photo by Conchi Martinez / Shutterstock.com)

Hyatt is based in Chicago and has a ton of excellent properties throughout the city. You can use your World of Hyatt points to stay at the ultra-cool Chicago Athletic Association. Even better, it's right across the street from Grant Park and home to multiple bars and restaurants, including The Milk Room, which serves some of the city's rarest liquors.

These are the closest Hyatt hotels to Lollapalooza:

  • Chicago Athletic Association: 15,000 points per night
  • Hyatt Centric, The Loop: 15,000 points per night
  • Hyatt Place Chicago Downtown: 15,000 points per night
  • Hyatt Regency Chicago: 12,000 points per night
  • Park Hyatt Chicago: 25,000 points per night

You can transfer Chase Ultimate Rewards points to World of Hyatt or earn with the Hyatt cobranded credit card.

  • World of Hyatt Credit Card: Earn 30,000 bonus points after spending $3,000 on purchases within the first 3 months from account opening. Plus, up to 30,000 more bonus points by earning 2 bonus points total per $1 spent on purchases that normally earn 1 Bonus Point, on up to $15,000 in the first six months of account opening.

Related: Earning two years of rewarding top-tier Hyatt elite status after just 11 nights

IHG hotels near Lollapalooza

From Kimpton to InterContinental, you'll find all of IHG's top brands in Chicago. (Photo by elesi / Shutterstock.com)

IHG has a handful of great properties in Chicago, with one of my favorites being the Kimpton Hotel Monaco Chicago. It's less than a half-mile from the festival and has newly-renovated rooms. Plus, there's a nightly wine happy hour and free coffee and tea in the morning.

Here's a look at all your IHG options in Chicago. Like Hilton, IHG Rewards prices award nights dynamically, so the prices below are for the Friday night of Lollapalooza.

  • InterContinental Hotels Chicago Magnificent Mile: 40,000 points per night
  • Holiday Inn Chicago Merchandise Mart Plaza: 20,000 points per night
  • Kimpton Gray Hotel: 39,000 points per night
  • Kimpton Monaco Chicago: 37,000 points per night

Earn IHG Rewards points with one of these credit cards:

Related: Maximizing redemptions with the IHG Rewards Club program

Marriott hotels near Lollapalooza

The JW Marriott is a high-end option nearby Grant Park. (Photo by Sorbis / Shutterstock.com)

Marriott is opening a new hotel in Chicago — the Le Méridien Essex — and it's right across Grant Park. Or, if you want a life of luxury after the festival, you might consider redeeming Marriott Bonvoy points at the nearby JW Marriott.

These are all the Marriott options around Grant Park:

  • The Blackstone, Autograph Collection: 40,000 points per night
  • JW Marriott Chicago: 60,000 points per night
  • Le Méridien Essex Chicago: 40,000 points per night
  • Renaissance Chicago Downtown: 60,000 points per night

You can earn Marriott Bonvoy points with the following credit cards:

Radisson hotels near Lollapalooza

The Radisson Blu Aqua is a high-end option north of Grant Park. (Image courtesy of Radisson)

Radisson's flagship Radisson Blu Aqua Hotel is nearby Grant Park and is one of Chicago's most iconic hotels, largely because of its design. Rooms are well laid out and have a very modern feel, and the business lounge will keep you energized with coffee and breakfast before the festival. A room at the Radisson Blu Aqua costs 70,000 Radisson Rewards points per night.

You can earn Radisson Rewards points with a Radisson cobranded credit card:

  • Radisson Rewards Premier Visa Signature® Card: Earn 50,000 points after your first purchase plus 35,000 points once you spend $2,500 on your card within the first 90 days of account opening
  • Radisson Rewards Visa® Card: Earn 30,000 bonus points after you spend $1,000 on your card within the first 90 days of account opening

The information for the Radisson Cards has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Related: 9 mistakes to avoid when redeeming hotel points

Ground transportation in Chicago

Chicago's L train is a fast and cheap way to get around the city. (Photo by Sergey Novikov / Shutterstock.com)

You can take Chicago's CTA Blue Line from O'Hare to downtown and the Orange Line from Midway to downtown. You'll pay $5 to take the train (referred to as the "L") from the airport to the city and $2.50 to return to the airport. You can purchase a train ticket (known as a Ventra card) at any CTA station or tap a contactless credit card at any turnstile.

Alternatively, you can take Uber, Lyft or a local taxi from the airport to the city. As someone who has done this commute hundreds of times, I always recommend taking the train if you're headed downtown from the airport. It's cheaper and often faster if traffic is heavy. Plus, both airports are directly connected to the train.

You can use the Capital One Venture card to cover your ground transportation fees. You can redeem miles at a fixed value of 1.0 cents per point toward any travel expense, so a $30 Uber ride costs 3,000 miles and a $200 plane ticket costs 20,000 points.

Related: What’s the fastest way to O’Hare in Chicago?

What card should I use to buy Lollapalooza tickets?

You'll want to use a credit card that offers bonus points on everyday spending to earn the most points when you buy Lollapalooza tickets. Some of these cards include:

Related: How to hit your card’s minimum spending bonus

Bottom line

Lollapalooza is one of the country's largest music festivals, and as a Chicago native, I'm happy to see it make a post-pandemic comeback. Here, I showed you how to book your trip to Lollapalooza with points and miles. It's hard to get around paying for your ticket, but you can use points and miles to offset the rest of the cost.

Feature photo by Ted Alexander Somerville / Shutterstock.com

For rates and fees of the Amex Green card, click here.
For rates and fees of the Amex Gold card, click here.
For rates and fees of the Amex Platinum card, click here.

Featured image by (Photo by Ted Alexander Somerville / Shutterstock.com)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.