In January 2014, the Chicago Red Stars announced that Press would be joining their roster for the 2014 season following the conclusion of her time with Tyresö in the 2013–14 Champions League. After Press joined the team in late May (two months into the 2014 NWSL season), she scored a team-high of six goals while playing in only 12 matches and was awarded the team's Golden Boot. During a match on July 4 against reigning champions Portland Thorns FC at Providence Park, she scored two goals in the last fifteen minutes to equalize the score, after being down 2–0 at halftime. On August 16, she scored another brace with goals in the 17th and 60th minutes helping Chicago draw 3–3 against Western New York Flash. Chicago finished fifth during the regular season with a 9–7–8 record. Press was named to the league's second XI team by players, coaches, and media.
Press scored a career-high 11 goals (and ranked third-best on the national team) in 2014. During a group stage match against Argentina at the 2014 International Tournament of Brasília, she scored four goals helping the U.S. win 7–0, and qualify for the championship game. Earlier in the year, she scored a goal against Russia in a friendly on February 8, 2014 and again on February 13, 2014. She was selected by national team head coach Tom Sermanni to play at the 2014 Algarve Cup. In October, Press featured in the 2014 CONCACAF Women's Championship where the team won the tournament.
Press has appeared in several advertisements and promotional pieces for Nike. In 2014, she was featured in a promo for Wheaties. In May 2015, she starred in television commercials for Coppertone. She became a brand ambassador for nutritional product manufacturer Genesis Today in February 2016. In January 2018, she partnered with Hydrive Energy Water.