According to Appendix B-The Tale of Years from The Lord of the Rings, Frodo left Bag End September 23, 3018 of the Third Age.
Frodo reached the Morgul Road at dusk on March 9, and passed the Crossroads and Minas Morgul the next day. On March 13, he was captured by orcs and taken to the tower of Cirith Ungol, a tower in the Ephel Duath (Mountains of Shadow), the mountains that bordered Mordor to the West.
Frodo and Sam escaped from Cirith Ungol March 14, 3019, and began their journey along the Morgai, the smaller mountain chain behind the Ephel Duath. Three days later, on the 18th, Frodo had crossed the Morgai, and was caught on the road to Udun in the north of Mordor.
So it depends on where you consider Frodo to have entered Mordor. If he reached Mordor March 10, when he passed Minas Morgul, it took 5, 30 day months and 17 days. If he reached Mordor March 13, when he was taken to Cirith Ungol (or before that, on 12th, in Shelob's lair), it took 5 months, 20 days to reach Cirith Ungol, and 5 months, 22 days to cross the Morgai.
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The exact length of time is not known, but the chronology indicates that the two of them fought for ten days. Gandalf fell at the bridge on January 15th and cast down the Balrog on the 25th. As Gandalf said, 'We fought far under the living earth, where time is not counted.'
Until the end of The Return of the King, when he went to the Undying Lands with the elves and Frodo.
They enter in pairs because Gandalf tells them to do it. They don't want to go in all at once, so Beorn will think they were trying to kill him The dwarves must enter Beorn's house in pairs so that, as Gandalf tells their tale to Beorn, each entrance does not seem very imposing and Beorn's interest in the story is built up. Then the group will be able to stay with Beorn.
The coincidence that helps the dwarves during their stay at Rivendell is when the moon comes out while Elrond is looking at the map. It has moon runes on it with extra information. This helps them along the journey to get to the treasure.
They have several stops where they get out of the weather and get some sleep. They go to Rivendell once. They stay at Beorn's house. They stay in a cave but that turns out to be a bad idea because they get kidnapped by goblins.
Gandalf is worried that Smaug may become an ally to the newly returned Sauron.